1242772-59-3Relevant articles and documents
Catalytic C-H bond stannylation: A new regioselective pathway to C-Sn bonds via C-H bond functionalization
Doster, Meghan E.,Hatnean, Jillian A.,Jeftic, Tamara,Modi, Sunjay,Johnson, Samuel A.
, p. 11923 - 11925 (2010)
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.