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

ABSTRACT: Racemic and scalemic ?-(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.

SUBMITTER: Goli M

PROVIDER: S-EPMC3021624 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

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

Goli Mohan M He Anyu A Falck J R JR

Organic letters 20101209 2

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. ...[more]

PMID: 21141984

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