Addition of bifunctional organoboron reagents to strained alkenes. Carbon-carbon bond formation with Rh(I) catalysis in aqueous media.
Arylboronate esters bearing a pendant Michael-type acceptor olefin undergo transmetalation with a rhodium-based catalytic complex to generate a functionalized organorhodium intermediate that can cyclize onto strained olefins in good to excellent yields. The catalytic system involves the use of an electron-rich, sterically bulky ligand to stabilize the organorhodium intermediate and reduce the incidence of protodeboronation in aqueous media.
Lautens
Mark
M
Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada. mlautens@chem.utoronto.ca
Mancuso
John
J