Hindered biaryls by C–H coupling: bisoxazoline-Pd catalysis leading to enantioselective C–H coupling
Chemical SciencePublished 1 January 2012
Kazuya Yamaguchi, Junichiro Yamaguchi, Armido Studer, Kenichiro Itami
Citations223
SJR quartileQ1
SJR score2.14
SNIP1.46
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
TL;DR
The newly established Pd(OAc)2/bisoxazoline/TEMPO system not only enables the synthesis of sterically hindered heterobiaryls but also offers an opportunity for enantioselective biaryl coupling through C–H functionalization.
Abstract
A new Pd-catalyzed C–H/C–B coupling of sterically hindered heteroarenes and arylboronic acids has been identified. The newly established Pd(OAc)2/bisoxazoline/TEMPO system not only enables the synthesis of sterically hindered heterobiaryls but also offers an opportunity for enantioselective biaryl coupling through C–H functionalization.
Keywords
Chemistry
Chemical ReviewsPalladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
12,693 Citations1995Norio Miyaura, Akira Suzuki
Journal of Medicinal ChemistryEscape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success
4,358 Citations2009Frank Lovering, Jack Bikker +1 more
It is demonstrated that saturation correlates with solubility, an experimental physical property important to success in the drug discovery setting, and both complexity and the presence of chiral centers correlate with success as compounds transition from discovery, through clinical testing, to drugs.
Angewandte Chemie International EditionPalladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reactions: Versatility and Practicality
4,100 Citations2009Xiao Chen, Keary M. Engle +2 more
Chemical ReviewsAryl−Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation
3,607 Citations2007Dino Alberico, Mark E. Scott +1 more
A number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, but the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps.
Angewandte Chemie International EditionTransition‐Metal‐Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage
2,738 Citations2009Lutz Ackermann, R. Vicente +1 more
P palladium and ruthenium catalysts have been described that enable the direct arylation of (hetero)arenes with challenging coupling partners--including electrophilic aryl chlorides and tosylates as well as simple arenes in cross-dehydrogenative arylations.
Angewandte Chemie International EditionPalladium‐Catalyzed Cross‐Coupling Reactions in Total Synthesis
2,691 Citations2005K. C. Nicolaou, Paul G. Bulger +1 more
In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Angewandte Chemie International EditionPalladium-Catalyzed Coupling Reactions of Aryl Chlorides
2,685 Citations2002Adam F. Littke, Gregory C. Fu
This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.
Accounts of Chemical ResearchPalladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands
2,610 Citations2008Rubén Martı́n, Stephen L. Buchwald
NatureCatalytic C–H functionalization by metal carbenoid and nitrenoid insertion
2,306 Citations2008Huw M. L. Davies, James R. Manning
Several facets of these kinds of C–H functionalization reactions are discussed and a perspective on how this methodology has affected the synthesis of complex natural products and potential pharmaceutical agents are provided.
Accounts of Chemical ResearchEvolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides
1,844 Citations2008John F. Hartwig
The conceptual basis and utility of the latest, "fourth-generation" palladium catalyst for the coupling of amines and related reagents with aryl halides is described and the effects of electronic properties on C-C and C-N bond-forming reductive elimination are similar.
Journal of the American Chemical SocietyCatalysts for Suzuki−Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure
1,775 Citations2005Timothy E. Barder, Shawn D. Walker +2 more
Structural studies of various 1.Pd complexes are presented along with computational data that help elucidate the efficacy that 1 imparts on Suzuki-Miyaura coupling processes, and a comparison of the reactions is presented that is informative in determining the relative importance of ligand bulk and electron-donating ability in the high activity of catalysts derived from ligands of this type.
Journal of the American Chemical SocietyVersatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions
1,588 Citations2000Adam F. Littke, Chaoyang Dai +1 more
Journal of the American Chemical SocietyHighly Active Palladium Catalysts for Suzuki Coupling Reactions
1,120 Citations1999John P. Wolfe, Robert A. Singer +2 more
ScienceThe Catalytic Cross-Coupling of Unactivated Arenes
1,013 Citations2007David R. Stuart, Keith Fagnou
P palladium, in conjunction with a copper oxidant, can catalyze the cross-coupling of N-acetylindoles and benzenes in high yield and high regioselectivity across a range of indoles without recourse to activating groups.
Accounts of Chemical ResearchDirect Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond Activation
963 Citations2008Jared C. Lewis, Robert G. Bergman +1 more
The relevant mechanistic insights that enabled synthetic advances and distinguished the resulting transformations from other methods are emphasized and researchers will better understand the details of the aforementioned Rh-catalyzed C-H bond functionalization reactions, resulting in the design of more efficient and robust catalysts, expanded substrate scope, and new transformations.
Journal of the American Chemical SocietyOxidative C−H Activation/C−C Bond Forming Reactions: Synthetic Scope and Mechanistic Insights
792 Citations2005Dipannita Kalyani, Nicholas R. Deprez +2 more
A new palladium-catalyzed method for C-H activation/carbon-carbon bond formation with hypervalent iodine arylating agents and preliminary evidence is provided in support of an unusual mechanism involving a Pd(II)/Pd(IV) catalytic cycle.
SynthesisTransition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage
779 Citations2008Fumitoshi Kakiuchi, Takuya Kochi
ScienceLigand-Enabled Reactivity and Selectivity in a Synthetically Versatile Aryl C–H Olefination
738 Citations2009Dong‐Hui Wang, Keary M. Engle +2 more
An operationally simple, atom-economical, carboxylate-directed Pd(II)-catalyzed C–H olefination reaction with phenylacetic acid and 3-phenylpropionic acid substrates, using oxygen at atmospheric pressure as the oxidant.
Angewandte Chemie International EditionPd<sup>II</sup>‐Catalyzed Enantioselective Activation of C(sp<sup>2</sup>)H and C(sp<sup>3</sup>)H Bonds Using Monoprotected Amino Acids as Chiral Ligands
672 Citations2008Bing‐Feng Shi, Nathan Maugel +2 more
A proof of concept is demonstrated by the design of a Pd/amino acid complex capable of catalyzing asymmetric activation of prochiral C H and C(sp) H bonds to form chiral products with new C C bonds in excellent enantioselectivity.
Angewandte Chemie International EditionNitroxides: Applications in Synthesis and in Polymer Chemistry
645 Citations2011L. Tebben, Armido Studer
Alkoxyamines derived from nitroxides are shown to be highly useful precursors of C-centered radicals in synthesis and also in polymer chemistry, and new developments in the synthesis of complex polymer architectures are highlighted.
Angewandte Chemie International Edition in EnglishLigand‐Accelerated Catalysis
600 Citations1995David J. Berrisford, Carsten Bolm +1 more
Journal of the American Chemical SocietyA General Method for Copper-Catalyzed Arylation of Arene C−H Bonds
593 Citations2008Hien‐Quang Do, R. Kashif M. Khan +1 more
A general method for copper-catalyzed arylation of sp (2) C-H bonds with p K a's below 35 has been developed and two arylcopper-phenanthroline complex intermediates were independently synthesized.
Chemistry - A European JournalConstruction of Nitrogen‐Containing Heterocycles by CH Bond Functionalization
541 Citations2009Praew Thansandote, Mark Lautens
An emerging interest among synthetic chemists is to use C-H functionalization to construct the nitrogen-containing core of these heterocycles with respect to the type of C- H bond functionalized.
Journal of the American Chemical SocietyPalladium-Catalyzed Alkylation of sp<sup>2</sup> and sp<sup>3</sup> C−H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C−H Activation Pathways
535 Citations2006Xiao Chen, Charles E. Goodhue +1 more
A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner.
Journal of the American Chemical SocietyA General Method for the Suzuki−Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides: Synthesis of Di- and Tri-ortho-substituted Biaryls in 2-Propanol at Room Temperature
530 Citations2003Oscar Navarro, Roy A. Kelly +1 more
The catalytic formation of di- and trisubstituted ortho biaryl junctions has been achieved using a palladacylce pre-catalyst bearing a N-heterocyclic carbene ligand.
Journal of the American Chemical SocietyLigand-Accelerated C−H Activation Reactions: Evidence for a Switch of Mechanism
479 Citations2010Keary M. Engle, Dong‐Hui Wang +1 more
Evidence is presented from intermolecular competition studies and kinetic isotope effect experiments that implies that the observed rate increases are a result of acceleration in the C-H cleavage step, and suggests that the origin of this phenomenon is a change in the mechanism of C- H cleavage from electrophilic palladation to proton abstraction.
Angewandte Chemie International EditionAn N‐Heterocyclic Carbene Ligand with Flexible Steric Bulk Allows Suzuki Cross‐Coupling of Sterically Hindered Aryl Chlorides at Room Temperature
468 Citations2003Gereon Altenhoff, Richard Goddard +2 more
Journal of the American Chemical SocietyA Catalytic Asymmetric Suzuki Coupling for the Synthesis of Axially Chiral Biaryl Compounds
466 Citations2000Jingjun Yin, Stephen L. Buchwald
Journal of the American Chemical SocietyPalladium-Catalyzed Alkylation of Aryl C−H Bonds with sp<sup>3</sup> Organotin Reagents Using Benzoquinone as a Crucial Promoter
416 Citations2005Xiao Chen, Jiao‐Jie Li +3 more
The combination of directed C-H activation, batch-wise addition of tetraalkyltin reagents, and rate enhancement by benzoquinone and microwave irradiation provides a promising strategy for the direct coupling of C- H bonds with organometallic reagents.
Journal of the American Chemical SocietyPd(II)-Catalyzed Enantioselective C–H Activation of Cyclopropanes
406 Citations2011Masayuki Wasa, Keary M. Engle +3 more
These results provide a new retrosynthetic disconnection for the construction of enantioenriched cis-substituted cyclopropanecarboxylic acids.
Accounts of Chemical ResearchStereoselective Total Synthesis of Axially Chiral Natural Products via Biaryl Lactones
380 Citations2001Gerhard Bringmann, Dirk Menche
The "lactone concept" provides an efficient strategy for the regio- and stereoselective construction of even bulky biaryls and is demonstrated in the total synthesis of selected representatives from five very different classes of natural biaryl products.
SynthesisTransition-Metal-Catalyzed Regioselective Arylation and Vinylation of Carboxylic Acids
377 Citations2010Tetsuya Satoh, Masahiro Miura
Journal of the American Chemical SocietyNickel-Catalyzed C–H/C–O Coupling of Azoles with Phenol Derivatives
376 Citations2011Kei Muto, Junichiro Yamaguchi +1 more
With this C-H/C-O biaryl coupling, this work synthesized a series of privileged 2-arylazoles, including biologically active alkaloids, and demonstrated the utility of the present reaction for functionalizing estrone and quinine.
Journal of the American Chemical SocietyVersatile Pd(II)-Catalyzed C−H Activation/Aryl−Aryl Coupling of Benzoic and Phenyl Acetic Acids
332 Citations2008Dong‐Hui Wang, Tian‐Sheng Mei +1 more
The use of aryltrifluoroborates as coupling partners and O(2) as the oxidant substantially improves the scope and practicality of the Pd-catalyzed C-H activation/C-C coupling reaction.
Angewandte Chemie International EditionEnantioselective CH Amination Using Cationic Ruthenium(II)–pybox Catalysts
316 Citations2008Erika M. Milczek, Nadège Boudet +1 more
The modular nature of the ligand, and the fact that the anionic ligands were independent of the chiral pybox ligand offered an opportunity which had not been possible by using either dirhodium(II)or porphyrin-based catalyst systems to address the challenge of catalytic asymmetric C H amination.
Journal of the American Chemical SocietyDirect C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis
315 Citations2006Shuichi Yanagisawa, Tomoko Sudo +2 more
A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed to afford a range of biaryls in good to excellent yields with high regioselectivity.
Angewandte Chemie International EditionFused Indolines by Palladium‐Catalyzed Asymmetric CC Coupling Involving an Unactivated Methylene Group
310 Citations2011Masafumi Nakanishi, Dmitry Katayev +2 more
Bulky, thermally stable, chiral palladium complexes generated from N-heterocyclic carbenes (NHCs) were successfully applied to the synthesis of highly enantioenriched trans-fused indolines.
Journal of the American Chemical SocietyA Chiral Rhodium Carboxamidate Catalyst for Enantioselective C−H Amination
304 Citations2008David N. Zalatan, J. Du Bois
Rh2(S-nap)4, a chiral dirhodium tetracarboxamidate complex, has been developed and shown to be an effective catalyst for the asymmetric, intramolecular C-H amination of sulfamate esters.
Chemical Society ReviewsAtropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics
304 Citations2001Paul Lloyd‐Williams, Ernest Giralt
Recent progress in the chemistry of the Suzuki coupling suggests that this constitutes a very powerful and general method for the synthesis of peptide biphenyls.
Organic LettersNickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates
303 Citations2009J. Canivet, Junichiro Yamaguchi +2 more
Ni-based catalytic systems for the arylation of heteroarenes with aryl halides and triflates have been established and a rapid synthesis of febuxostat, a drug for gout and hyperuricemia, is demonstrated.
Chemical CommunicationsThe first asymmetric Suzuki cross-coupling reaction
298 Citations2000Andrew N. Cammidge, Karen V. L. Crépy
Journal of the American Chemical SocietyHighly Efficient and Enantioselective Cyclization of Aromatic Imines via Directed C−H Bond Activation
291 Citations2004Reema K. Thalji, Jonathan A. Ellman +1 more
The first highly enantioselective catalytic reaction involving aromatic C-H bond activation is communicated and the identified catalyst system enables the intramolecular alkylation reaction to be performed at temperatures 75 degrees C lower than the previously reported achiral system.
Journal of the American Chemical SocietyEnantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki−Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations
284 Citations2010Xiaoqiang Shen, Gavin O. Jones +3 more
This work reports efficient syntheses of axially chiral biaryl amides in yields ranging from 80-92%, and with enantioselectivity in the range 88-94% ee employing an asymmetric Suzuki-Miyaura process with Pd(OAc)(2) and KenPhos as ligand, and demonstrates that axiallyChiral heterocyclic and biphenyl compounds can also be synthesized with this methodology.
Journal of the American Chemical SocietyEnantioenriched Synthesis of <i>C</i><sub>1</sub>-Symmetric BINOLs: Iron-Catalyzed Cross-Coupling of 2-Naphthols and Some Mechanistic Insight
259 Citations2010Hiromichi Egami, Kenji Matsumoto +3 more
Highly enantioselective aerobic oxidative cross-coupling of 2-naphthols with broad substrate scope was achieved using an iron(salan) complex as the catalyst.
The Journal of Organic ChemistryPerspective on Dirhodium Carboxamidates as Catalysts
256 Citations2006Michael P. Doyle
With chiral carboxamidate ligands these dirhodium compounds show exceptional enantiocontrol for intramolecular cyclopropanation and carbon-hydrogen insertion reactions of diazoacetates, and they are also highly efficient and selective for hetero-Diels-Alder reactions.
Journal of the American Chemical SocietyProgrammed Synthesis of Tetraarylthiophenes through Sequential C−H Arylation
250 Citations2009Shuichi Yanagisawa, Kirika Ueda +2 more
A general protocol for the programmed synthesis of tetraarylthiophenes has been established and interesting metal- and ligand-controlled regiodivergent C-H arylations have been uncovered.
Angewandte Chemie International EditionA General Catalyst for the β‐Selective C–H Bond Arylation of Thiophenes with Iodoarenes
244 Citations2010Kirika Ueda, Shuichi Yanagisawa +2 more
Angewandte Chemie International EditionAsymmetric Suzuki–Miyaura Coupling in Water with a Chiral Palladium Catalyst Supported on an Amphiphilic Resin
240 Citations2009Yasuhiro Uozumi, Yutaka Matsuura +2 more
The chiral imidazoindole phosphine-palladium catalyst supported on an amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin could be recycled readily.
Tetrahedron AsymmetryAtropselective alkylation of biaryl compounds by means of transition metal-catalyzed C–H/olefin coupling
238 Citations2000Fumitoshi Kakiuchi, Pierre Le Gendre +3 more
Angewandte Chemie International EditionAsymmetric Suzuki–Miyaura Coupling Reactions Catalyzed by Chiral Palladium Nanoparticles at Room Temperature
235 Citations2008Koji Sawai, Ryouta Tatumi +2 more
Angewandte Chemie International EditionOxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise Difficult C4‐Selective CH Arylation Enabled by Boronic Acids
227 Citations2011Sylvia Kirchberg, Satoshi Tani +4 more
It is reported that the Pd-catalyzed oxidative C H arylation of thiophenes and thiazoles with arylboronic acids manifests the otherwise difficult C4 regioselectivity.
Journal of the American Chemical Society<i>C</i><sub>2</sub>-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki−Miyaura Cross-Coupling
226 Citations2008Antonio Bermejo Gómez, Abel Ros +2 more
The high catalytic activity of the [PdCl2(bis-hydrazone)] complex allows reactions to be performed at room temperature, affording products with excellent enantioselectivities in all cases.
Angewandte Chemie International EditionEnantioselective Palladium‐Catalyzed Direct Arylations at Ambient Temperature: Access to Indanes with Quaternary Stereocenters
217 Citations2009Martin R. Albicker, Nicolai Cramer
Pd-catalyzed enantioselective intramol direct arylation of vinyl triflates using tailored TADDOL-based phosphoramidite ligands provides indanes, e.g. I, with quaternary stereocenters.
Angewandte Chemie International EditionIridium Catalysis for CH Bond Arylation of Heteroarenes with Iodoarenes
211 Citations2009Benoît Join, Takuya Yamamoto +1 more
The dramatic ligand effect on reaction efficiency leads to the discovery that Crabtree's catalyst (see scheme) is the optimal catalyst precursor.
Chemistry - A European JournalNickel‐Catalyzed CH Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules
208 Citations2011Takuya Yamamoto, Kei Muto +4 more
This newly developed methodology has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the Treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity).
Angewandte Chemie International EditionPalladium‐Catalyzed β Arylation of Carboxylic Esters
206 Citations2010Alice Renaudat, Ludivine Jean‐Gérard +4 more
A diversion from the palladium(0) catalysis mechanism is described and the development of a straightforward and conceptually new b-C H arylation method is described, which is complementary to directing-group-controlled b arieslation reactions.
Chemical CommunicationsEnantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)–H activation/cyclisation
189 Citations2011Saithalavi Anas, Alex Cordi +1 more
The first example of the enantioselective methyl C-H activation by an intramolecular ArPdX species and subsequent cyclisation was developed.
Chemistry - A European Journal[Pd(IPr*)(cinnamyl)Cl]: An Efficient Pre‐catalyst for the Preparation of Tetra‐<i>ortho</i>‐substituted Biaryls by Suzuki–Miyaura Cross‐Coupling
185 Citations2012Anthony Chartoire, Mathieu Lesieur +5 more
IPr* is reported as the largest N-heterocyclic carbene (NHC) to date for [Pd(NHC)(cin)Cl] complexes, explaining the high reactivity observed for this complex in this challenging transformation.
Journal of the American Chemical SocietyLigand-Accelerated Cross-Coupling of C(sp<sup>2</sup>)–H Bonds with Arylboron Reagents
182 Citations2011Keary M. Engle, Peter Thuy-Boun +2 more
A ligand-accelerated Pd(II)-catalyzed C(sp(2))-H/arylboron cross-coupling reaction of phenylacetic acid substrates with aryltrifluoroborates is reported.
Angewandte ChemieHighly Enantioselective Synthesis of Axially Chiral Biarylphosphonates: Asymmetric Suzuki–Miyaura Coupling Using High‐Molecular‐Weight, Helically Chiral Polyquinoxaline‐Based Phosphines
177 Citations2011Takeshi Yamamoto, Yuto Akai +2 more
Angewandte Chemie International EditionEnantioselective Intramolecular Benzylic CH Bond Amination: Efficient Synthesis of Optically Active Benzosultams
156 Citations2011Masami Ichinose, Hidehiro Suematsu +4 more
'Salen' along: the iridium(III)-salen complex 1 efficiently catalyzes the title reaction of 2-ethylbenzenesulfonyl azides to give five-membered sultams with high enantioselectivity.
Journal of the American Chemical SocietyDirect Arylation of Polycyclic Aromatic Hydrocarbons through Palladium Catalysis
156 Citations2011K. Mochida, Katsuaki Kawasumi +2 more
Journal of the American Chemical SocietySynthesis of Dragmacidin D via Direct C–H Couplings
156 Citations2011Debashis Mandal, Atsushi Yamaguchi +2 more
A concise total synthesis of dragmacidin D is established using direct C-H coupling reactions and the two indole-pyrazinone bonds and the presence of a polar aminoimidazole unit are established.
Nature Reviews Drug DiscoveryThe influence of the 'organizational factor' on compound quality in drug discovery
154 Citations2011Paul D. Leeson, Stephen A. St-Gallay
It is concluded that a substantial sector of the pharmaceutical industry has not modified its drug design practices and is still producing compounds with suboptimal physicochemical profiles.
Chemistry - A European JournalEfficient Synthesis of Chiral 1,1′‐Binaphthalenes by the Asymmetric Suzuki–Miyaura Reaction: Dramatic Synthetic Improvement by Simple Purification of Naphthylboronic Acids
142 Citations2006Miroslav Genov, Antonio Almorı́n +1 more
A very simple purification prior to their use in Suzuki-Miyaura couplings has been found to be crucial, rendering efficient some reactions that had been reported in the literature either to fail or to give extremely poor yields.
OrganometallicsPalladium Complexes of Planar Chiral Ferrocenyl Phosphine-NHC Ligands: New Catalysts for the Asymmetric Suzuki−Miyaura Reaction
133 Citations2010Nathalie Debono, Agnès Labande +3 more
Air-stable neutral and cationic palladium complexes bearing chiral phosphine-N-heterocyclic carbene ligands with planar chirality have been shown to catalyze the asymmetric coupling of aryl bromides with aRYlboronic acids in good yields and moderate enantioselectivities.
Chemistry LettersOxidative C–H/C–H Coupling of Azine and Indole/Pyrrole Nuclei: Palladium Catalysis and Synthesis of Eudistomin U
126 Citations2011Atsushi Yamaguchi, Debashis Mandal +2 more
Topics in current chemistryRhodium-Catalyzed C–H Bond Arylation of Arenes
124 Citations2009Jean Bouffard, Kenichiro Itami
A review is presented of synthetic methods for the preparation of biaryls by the rhodium-catalyzed C-H bond arylation of arenes with aryl halides with an emphasis on postulated mechanisms and their implications on reactivity, selectivity and substrate scope.
Organic LettersChiral Diene as the Ligand for the Synthesis of Axially Chiral Compounds via Palladium-Catalyzed Suzuki−Miyaura Coupling Reaction
118 Citations2010Shu-Sheng Zhang, Zhi-Qian Wang +2 more
The first palladium-diene-catalyzed asymmetric Suzuki-Miyaura coupling reaction has been achieved and a number of functionalized biaryls were obtained in high yields and in moderate to high enantioselectivities.
Angewandte Chemie International EditionA Polymer‐Supported Chiral Dirhodium(II) Complex: Highly Durable and Recyclable Catalyst for Asymmetric Intramolecular CH Insertion Reactions
117 Citations2010Koji Takeda, Tadashi Oohara +3 more
The Journal of Organic ChemistryAsymmetric Synthesis of an Axially Chiral Antimitotic Biaryl via an Atropo-Enantioselective Suzuki Cross-Coupling
109 Citations2003Audrey Herrbach, Angéla Marinetti +3 more
This work gives the first application of the asymmetric Suzuki coupling to a biologically relevant target, furnishing the nonbridged biaryl (-)-6, precursor of (-)-2, with up to 40% ee using binaphthyl ligand 7a.
Angewandte Chemie International EditionEnantioselective Suzuki Reactions: Catalytic Asymmetric Synthesis of Compounds Containing Quaternary Carbon Centers
95 Citations2004Michael C. Willis, Luke H. Powell +2 more
Journal of Medicinal ChemistryDesign, Synthesis, and Biological Activity of Potent and Orally Available G Protein-Coupled Receptor 40 Agonists
87 Citations2011Shinobu Sasaki, Shuji Kitamura +16 more
The pharmacological results suggest that GPR40 agonists might be novel glucose-dependent insulin secretagogues with little or no risk of hypoglycemia.
Angewandte Chemie International EditionSynthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross‐Coupling
61 Citations2011Jeffrey L. Gustafson, Daniel Lim +2 more
The preparation of single atropisomer scaffolds could lead to increases in potency for small molecules, through an increase in the effective concentration of the biologically active atrop isomer, with the exclusion of a less active, or alternatively active form.
…