Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates

Jérôme Canivet; Junichiro Yamaguchi; Ikuya Ban; Kenichiro Itami

doi:10.1021/ol9001587

Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates

Jérôme Canivet, Junichiro Yamaguchi, Ikuya Ban, Kenichiro Itami^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

273 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1733-1736
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	8
DOIs	https://doi.org/10.1021/ol9001587
Publication status	Published - 2009 Apr 16
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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T1 - Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates

AU - Canivet, Jérôme

AU - Yamaguchi, Junichiro

AU - Ban, Ikuya

AU - Itami, Kenichiro

PY - 2009/4/16

Y1 - 2009/4/16

N2 - 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.

AB - 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.

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Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates

Abstract

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