Ni-catalyzed Sonogashira coupling of nonactivated alkyl halides: orthogonal functionalization of alkyl iodides, bromides, and chlorides.
Ni-catalyzed Sonogashira coupling of nonactivated, beta-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, heterocycle, acetal, and aryl halide, in both coupling partners. The coupling can be selective for a specific C-X bond (X = I, Br, Cl) and allows for orthogonal functionalization of alkyl halides with multiple reactive sites.
Vechorkin
Oleg
O
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, SB-ISIC-LSCI, BCH 3305, Lausanne CH 1015, Switzerland.
Barmaz
Delphine
D
Proust
Valérie
V
Hu
Xile
X
D000473:Alkanes / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry; D006219:Halogens / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry; D009532:Nickel / Q000737:chemistry*
D000473:Alkanes; D006219:Halogens; D002713:Chlorine; D009532:Nickel; D007455:Iodine; D001966:Bromine