Stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

J R Falck; Paresh K. Patel; Anish Bandyopadhyay

doi:10.1021/ja064948q

Stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

J R Falck, Paresh K. Patel, Anish Bandyopadhyay

Biochemistry

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

50 Scopus citations

Abstract

Racemic and scalemic PTC-protected α-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, 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)	790-793
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	129
Issue number	4
DOIs	https://doi.org/10.1021/ja064948q
State	Published - Jan 31 2007

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "Racemic and scalemic PTC-protected α-hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using copper(I) thiophene-2-carboxylate (CuTC) in THF at or below room temperature. Simple aryl iodides and 1-iodocyclohexene, 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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Stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

Abstract

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