One-pot methylenation-hydroboration-cross-coupling reactions

ORGN 62

Chehla Ladjel, chehla.ladjel@umontreal.ca and Hélène Lebel, lebelhe@chimie.umontreal.ca. Département de Chimie, Université de Montréal, PO Box 6128 Station Downtown, Montréal, QC H3C3J7, Canada

Our research group has recently developed a new copper and rhodium catalysed methylenation of carbonyl derivatives using TMSCHN2, i-PrOH, Ph3P. We have recently reported two new cascade processes: a formal reductive one-carbon homologation via a rhodium-catalysed methylenation-hydrogenation cascade; and a methylenation-hydroboration cascade process leading to the corresponding organoborane product, wich can be further functionalized. Copper salts which are very efficient to catalyze the methylenation reaction are also known as co-catalyst for cross-coupling reactions; thus one-pot processes that combine olefination and cross-coupling reactions should be particularly efficient. Indeed we wish now to present a new multicatalytic methylenation –hydroboration–Suzuki-coupling one-pot process, which combined rhodium or copper and palladium catalysts. A synthetic strategy towards Abietanes will be also disclosed.

 

 

New Reactions and Methodology
1:30 PM-5:10 PM, Sunday, March 25, 2007 McCormick Place Lakeside -- Room E351, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007