Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n -butylstannanes with alkenyl, aryl, and heteroaryl electrophiles

Mohan Goli; Anyu He; J R Falck

doi:10.1021/ol102863u

Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n -butylstannanes with alkenyl, aryl, and heteroaryl electrophiles

Mohan Goli, Anyu He, J R Falck

Biochemistry

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

42 Scopus citations

Abstract

Racemic and scalemic α-(acyloxy)-tri-n-butylstannanes undergo Pd-catalyzed cross-couplings with alkenyl/aryl/heteroaryl iodides, bromides, and triflates in moderate to good yields in THF at 45 °C. Simple aryl iodides and unprotected aza-arenes, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl and stannyl-substituted stereocenters.

Original language	English (US)
Pages (from-to)	344-346
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	2
DOIs	https://doi.org/10.1021/ol102863u
State	Published - Jan 21 2011

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Racemic and scalemic α-(acyloxy)-tri-n-butylstannanes undergo Pd-catalyzed cross-couplings with alkenyl/aryl/heteroaryl iodides, bromides, and triflates in moderate to good yields in THF at 45 °C. Simple aryl iodides and unprotected aza-arenes, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl and stannyl-substituted stereocenters.",

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AU - Goli, Mohan

AU - He, Anyu

AU - Falck, J R

PY - 2011/1/21

Y1 - 2011/1/21

N2 - Racemic and scalemic α-(acyloxy)-tri-n-butylstannanes undergo Pd-catalyzed cross-couplings with alkenyl/aryl/heteroaryl iodides, bromides, and triflates in moderate to good yields in THF at 45 °C. Simple aryl iodides and unprotected aza-arenes, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl and stannyl-substituted stereocenters.

AB - Racemic and scalemic α-(acyloxy)-tri-n-butylstannanes undergo Pd-catalyzed cross-couplings with alkenyl/aryl/heteroaryl iodides, bromides, and triflates in moderate to good yields in THF at 45 °C. Simple aryl iodides and unprotected aza-arenes, two classes of electrophiles that typically react sluggishly, are also good substrates. Cross-couplings proceed with retention of configuration at the alkenyl and stannyl-substituted stereocenters.

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Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n -butylstannanes with alkenyl, aryl, and heteroaryl electrophiles

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