Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates

Santanu Panda; Joseph M. Ready

doi:10.1021/jacs.7b01410

Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates

Santanu Panda, Joseph M. Ready

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

82 Scopus citations

Abstract

Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.

Original language	English (US)
Pages (from-to)	6038-6041
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	17
DOIs	https://doi.org/10.1021/jacs.7b01410
State	Published - May 3 2017

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates",

abstract = "Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.",

author = "Santanu Panda and Ready, {Joseph M.}",

note = "Funding Information: Financial support provided by the NIH (R01GM102403) and the Welch Foundation (I-1612). X-ray crystallography performed by Dr. V. Lynch (UT Austin). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Ready, Joseph M.

N1 - Funding Information: Financial support provided by the NIH (R01GM102403) and the Welch Foundation (I-1612). X-ray crystallography performed by Dr. V. Lynch (UT Austin). Publisher Copyright: © 2017 American Chemical Society.

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N2 - Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.

AB - Boronic esters react with 2-lithiated indoles to form boronate intermediates. The boronate reacts with allylic acetates in the presence of (BINAP)Pd catalysts to allylate C3 concurrent with alkyl migration from B to C2 of the indole. Overall, the process is a three-component coupling that joins an allylic acetate, and indole and an organo-B(pin) species to provide substituted indoles and indolines with high enantio-, regio-, and diastereoselectivity.

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Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates

Abstract

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