Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters

Yuk Tai Tsoi; Zhongyuan Zhou; Wing Yiu Yu

doi:10.1021/ol2022577

Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters

Yuk Tai Tsoi, Zhongyuan Zhou, Wing Yiu Yu

Research output: Journal article publication › Journal article › Academic research › peer-review

72 Citations (Scopus)

Abstract

A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with R-aryldiazoacetates to form oxa-π-allylrhodium complexes. With KOtBu and alkyl halides, tandem alkylation of the allyl complex occurs to form a quaternary stereocenter at the carbenic carbon.

Original language	English
Pages (from-to)	5370-5373
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	19
DOIs	https://doi.org/10.1021/ol2022577
Publication status	Published - 7 Oct 2011

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2022577

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title = "Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters",

abstract = "A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with R-aryldiazoacetates to form oxa-π-allylrhodium complexes. With KOtBu and alkyl halides, tandem alkylation of the allyl complex occurs to form a quaternary stereocenter at the carbenic carbon.",

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Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters. / Tsoi, Yuk Tai; Zhou, Zhongyuan; Yu, Wing Yiu.
In: Organic Letters, Vol. 13, No. 19, 07.10.2011, p. 5370-5373.

Research output: Journal article publication › Journal article › Academic research › peer-review

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AB - A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with R-aryldiazoacetates to form oxa-π-allylrhodium complexes. With KOtBu and alkyl halides, tandem alkylation of the allyl complex occurs to form a quaternary stereocenter at the carbenic carbon.

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DO - 10.1021/ol2022577

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Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary r,r-heterodiaryl carboxylic esters

Abstract

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