Borrowing hydrogen: C-C bond formation from alcohols using a Xantphos ruthenium complex

ORGN 6

Paul A. Slatford, P.Slatford@bath.ac.uk and Jonathan M. J. Williams. Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom
The use of conventional toxic alkylating agents is becoming an arduous task due to changes in licensing and regulatory laws. The overall outline in Scheme 1 is appealing since carbon nucleophiles can be alkylated without the need to use such means. We used benzyl alcohol 1 and ketonitrile 2 as a model reaction for an oxidation-Knoevenagel-reduction reaction to provide alkylated product 3 (Scheme 2). The only by-product in this system is water. The best system was found to be a combination of Ru(PPh3)3(CO)H2 and Xantphos. In addition the scope of both the alcohol and the nucleophile has been explored and will be discussed.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 134, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006