PEPPSI-IPr: A user-friendly, easily employed cross-coupling pre-catalyst

ORGN 11

Michael G. Organ, organ@yorku.ca1, Cory Valente2, Christopher J. O'Brien2, Niloufar Hadei, organ@yorku.ca2, Igor Dubovyk, idubovyk@yorku.ca2, Stephanie Avola, stephanie.avola@rogers.com2, and Joanna Nasielski, yu251138@yorku.ca2. (1) Department of Chemistry, Toronto Total Synthesis, 291 Northshore Boulevard West, Burlington, ON L7T1A6, Canada, (2) Department of Chemistry, York University, 4700 Keele Street, Toronto, ON M3J 1P3, Canada
A continuing assessment of the scope and utility of an easily prepared, air and moisture stable Pd pre-catalyst (PEPPSITM-iPr) has been carried out. PEPPSITM-iPr has been exploited in Buchwald/Hartwig amination as well as in Kumada and Suzuki couplings. A variety of functionalized electrophiles have been coupled with an assortment of relatively elaborate organometallics/nucleophiles to effect several drug-like and synthetically interesting pre-cursors/products. These results continue to reveal a catalytic system possessing a greatly widened scope relative to previously set benchmarks within the field and is poised for many future successes. All told, significant progress has been made toward the goal of finding a truly robust and universal catalytic system.

 

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