Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/Triflates
Organic LettersPublished 18 March 2009
J. Canivet, Junichiro Yamaguchi, Ikuya Ban, Kenichiro Itami
Citations303
SJR quartileQ1
SJR score1.24
SNIP1.03
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TL;DR
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.
Abstract
Ni-based catalytic systems for the arylation of heteroarenes with aryl halides and triflates have been established. Ni(OAc)(2)/bipy is a general catalyst for aryl bromides/iodides, and Ni(OAc)(2)/dppf is effective for aryl chlorides/triflates. Thiazole, benzothiazole, oxazole, benzoxazole, and benzimidazole are applicable as heteroarene coupling partners. A rapid synthesis of febuxostat, a drug for gout and hyperuricemia, is also demonstrated.
Keywords
Chemistry
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SynthesisCross-Coupling Reactions for the Preparation of 2-Arylfurans, 2-Benzylfuran and 2-Cinnamylfuran
61 Citations1987Andrew Pelter, Martin Rowlands +1 more
Journal of Organometallic ChemistryPalladium- and nickel-catalyzed aryl- and acyl-demetallation of organometallic compounds
37 Citations1985Н. А. Бумагин, Andrey B. Ponomaryov +1 more
Chemistry - A European JournalNickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents
28 Citations2008Sarav B. Jhaveri, Kenneth R. Carter
The one-pot, one-step, nickel-catalyzed coupling of aryl bromides in the presence of alkyllithium reagents is reported, which is a powerful synthetic tool for the preparation of a wide range of specialty polymers, composite materials, and pharmaceutically active compounds.
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