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Rhodium-Catalyzed Methylenation of Aldehydes

Hélène Lebel* and Valérie Paquet

*Département de Chimie, Université de Montréal, C. P. 6128, Succursale Centre-Ville, Montréal, Québec, Canada H3C 3J7, Email: helene.lebelumontreal.ca

H. Lebel, V. Paquet, J. Am. Chem. Soc., 2004, 126, 320-328.

DOI: 10.1021/ja038112o (free Supporting Information)


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Abstract

A mild and nonbasic rhodium-catalyzed methylenation of aldehydes using trimethylsilyldiazomethane and triphenylphosphine in THF produces various terminal alkenes in excellent yields including enolizable keto aldehydes and nonracemic aldehydes. The use of an easily removable phosphine is also described.


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proposed mechanism



Copper-Carbene Complexes as Catalysts in the Synthesis of Functionalized Styrenes and Aliphatic Alkenes

H. Lebel, M. Davi, S. Díez-Gonzlez, S. P. Nolan, J. Org. Chem., 2007, 72, 144-149.

Reductive One-Carbon Homologation of Aldehydes and Ketones

H. Lebel, C. Ladjel, J. Org. Chem., 2005, 70, 10159-10161.

Multicatalytic Processes Using Diverse Transition Metals for the Synthesis of Alkenes

H. Lebel, V. Paquet, J. Am. Chem. Soc., 2004, 126, 11152-11153.


Key Words

Methylenation


ID: J48-Y2004-1360