Palladium-catalyzed synthesis and transformation of allylboronic acids

ORGN 268

Kalman J. Szabo, kalman@organ.su.se, Department of Organic Chemistry, Stockholm University, Stockholm, Sweden

We have devised an efficient palladium pincer-complex (2) catalyzed synthesis of allylboronic acids (1a) and allyl boronates (1b) using diboronic acid (3). This catalytic reaction has a very broad synthetic scope as allyl alcohols (4), allyl acetates (5), vinyl cyclopropenes (6) and vinyl aziridines (7) can be used as substrates. The reactions proceed with excellent regio and stereoselectivity and with a high level of functional group tolerance. The allylboronic acids (1a) and allyl boronates (1b) obtained in these reactions were employed as substrates in Suzuki-Miyaura type of coupling reactions, as well as in allylation of aldehydes and imines, including asymmetric catalysis.