Catalytic C-H bond stannylation: a new regioselective pathway to C-Sn bonds via C-H bond functionalization.
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.
Doster
Meghan E
ME
Department of Chemistry & Biochemistry, University of Windsor, Windsor, ON, Canada N9B 3P4.
Hatnean
Jillian A
JA
Jeftic
Tamara
T
Modi
Sunjay
S
Johnson
Samuel A
SA
D047250:Calixarenes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D014001:Tin / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D009942:Organometallic Compounds; D011725:Pyridines; D014753:Vinyl Compounds; D047250:Calixarenes; D014001:Tin; D009532:Nickel