Copper-facilitated Suzuki reactions: application to 2-heterocyclic boronates.
The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(I) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.
Deng
James Z
JZ
Department of Medicinal Chemistry, Merck Research Laboratories, P.O. Box 4, West Point, Pennsylvania 19486, USA. james_deng@merck.com
Paone
Daniel V
DV
Ginnetti
Anthony T
AT
Kurihara
Hideki
H
Dreher
Spencer D
SD
Weissman
Steven A
SA
Stauffer
Shaun R
SR
Burgey
Christopher S
CS
D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*
D001897:Boronic Acids; D006571:Heterocyclic Compounds; D003300:Copper