Cyclopropylmethylation of benzylic and allylic chlorides with cyclopropylmethylstannane catalyzed by gallium or indium halide.
Benzylic and allylic chlorides easily coupled with cyclopropylmethylstannane in the presence of GaCl(3) or InBr(3) catalyst, in which an intermediate of an active butenylgallium or -indium species was confirmed by NMR spectroscopy and X-ray analysis. An ionic reaction process is plausible for this coupling.
Kiyokawa
Kensuke
K
Department of Applied Chemistry, Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Yasuda
Makoto
M
Baba
Akio
A
D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D005708:Gallium / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D006843:Hydrocarbons, Chlorinated; D009947:Organotin Compounds; C550218:cyclopropylmethylstannane; D007204:Indium; C020758:indium trichloride; C034163:gallium chloride; D005708:Gallium