Nickel-catalyzed α-arylation of ketones with phenol derivatives

Ryosuke Takise; Kei Muto; Junichiro Yamaguchi; Kenichiro Itami

doi:10.1002/anie.201403823

Nickel-catalyzed α-arylation of ketones with phenol derivatives

Ryosuke Takise, Kei Muto, Junichiro Yamaguchi^*, Kenichiro Itami

^*Corresponding author for this work

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

149 Citations (Scopus)

Abstract

The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. For this transformation, 3,4-bis(dicyclohexylphosphino) thiophene (dcypt) was identified as a new, enabling, air-stable ligand for this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis. The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. The use of 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) as an air-stable ligand enables this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis.

Original language	English
Pages (from-to)	6791-6794
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	26
DOIs	https://doi.org/10.1002/anie.201403823
Publication status	Published - 2014 Jun 23
Externally published	Yes

Keywords

C-O activation
nickel
oxidative addition
synthetic methods
α-arylation

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201403823

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title = "Nickel-catalyzed α-arylation of ketones with phenol derivatives",

abstract = "The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. For this transformation, 3,4-bis(dicyclohexylphosphino) thiophene (dcypt) was identified as a new, enabling, air-stable ligand for this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis. The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. The use of 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) as an air-stable ligand enables this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis.",

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AU - Takise, Ryosuke

AU - Muto, Kei

AU - Yamaguchi, Junichiro

AU - Itami, Kenichiro

PY - 2014/6/23

Y1 - 2014/6/23

N2 - The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. For this transformation, 3,4-bis(dicyclohexylphosphino) thiophene (dcypt) was identified as a new, enabling, air-stable ligand for this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis. The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. The use of 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) as an air-stable ligand enables this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis.

AB - The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. For this transformation, 3,4-bis(dicyclohexylphosphino) thiophene (dcypt) was identified as a new, enabling, air-stable ligand for this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis. The nickel-catalyzed α-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful α-arylketones. The use of 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) as an air-stable ligand enables this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis.

KW - C-O activation

KW - nickel

KW - oxidative addition

KW - synthetic methods

KW - α-arylation

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Nickel-catalyzed α-arylation of ketones with phenol derivatives

Abstract

Keywords

ASJC Scopus subject areas

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