%0 Journal Article %A Doster, Meghan E. %A Hatnean, Jillian A. %A Jeftic, Tamara %A Modi, Sunjay %A Johnson, Samuel A. %D 2010 %T Catalytic C−H Bond Stannylation: A New Regioselective Pathway to C−Sn Bonds via C−H Bond Functionalization %U https://acs.figshare.com/articles/journal_contribution/Catalytic_C_H_Bond_Stannylation_A_New_Regioselective_Pathway_to_C_Sn_Bonds_via_C_H_Bond_Functionalization/2738080 %R 10.1021/ja105588v.s001 %2 https://acs.figshare.com/ndownloader/files/4415002 %K organotin compounds %K vinyl stannanes %K Bond %K vinyl compounds %K New Regioselective Pathway %K bond %X The ubiquitous Stille coupling reaction utilizes Sn−C bonds and is of great utility to organic chemists. Unlike the B−C bonds used in the Miyaura−Suzuki coupling reaction, which are readily obtained via direct borylation of C−H bonds, routes to organotin compounds via direct C−H bond functionalization are lacking. Here we report that the nickel-catalyzed reaction of fluorinated arenes and pyridines with vinyl stannanes does not provide the expected vinyl compounds via C−F activation but rather provides new Sn−C bonds via C−H functionalization with the loss of ethylene. This mechanism provides a new unanticipated methodology for the direct conversion of C−H bonds to carbon−heteroatom bonds. %I ACS Publications