4.4 Article

Rhodium-catalyzed addition of arylstannanes to carbon-heteroatom double bond

Journal

TETRAHEDRON
Volume 59, Issue 24, Pages 4351-4361

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(03)00586-6

Keywords

arylation; carbonyl compounds; imines; organotin compounds; rhodium catalyst

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The addition of arylstannanes to the carbon-heteroatom double bond in the presence of a catalytic amount of a cationic rhodium complex ([Rh(cod)(MeCN)(2)]BF4) was examined. The reactions of aldehydes, alpha-dicarbonyl compounds, and N-substituted aldimines with the arylstannanes gave corresponding alcohols, alpha-hydroxy carbonyl compounds, and amines, respectively. An arylrhodium complex generated by the transmetalation with the arylstannane was probably the active catalytic species. (C) 2003 Elsevier Science Ltd. All rights reserved.

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