Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

Chao Feng; Teck Peng Loh

doi:10.1021/ol501309e

Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

Chao Feng, Teck Peng Loh^*

^*Corresponding author for this work

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

31 Citations (Scopus)

Abstract

Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydroboration, it enables the formal anti-Markovnikov hydroamidation of terminal alkynes, stereospecifically affording the trans-enamides in excellent yields.

Original language	English
Pages (from-to)	3444-3447
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	13
DOIs	https://doi.org/10.1021/ol501309e
Publication status	Published - Jul 3 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol501309e

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title = "Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides",

abstract = "Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydroboration, it enables the formal anti-Markovnikov hydroamidation of terminal alkynes, stereospecifically affording the trans-enamides in excellent yields.",

author = "Chao Feng and Loh, {Teck Peng}",

year = "2014",

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doi = "10.1021/ol501309e",

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journal = "Organic Letters",

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T1 - Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

AU - Feng, Chao

AU - Loh, Teck Peng

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Y1 - 2014/7/3

N2 - Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydroboration, it enables the formal anti-Markovnikov hydroamidation of terminal alkynes, stereospecifically affording the trans-enamides in excellent yields.

AB - Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydroboration, it enables the formal anti-Markovnikov hydroamidation of terminal alkynes, stereospecifically affording the trans-enamides in excellent yields.

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M3 - Article

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JO - Organic Letters

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Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

Abstract

ASJC Scopus Subject Areas

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