Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes.
Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete gamma- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed.
Ohmiya
Hirohisa
H
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan. ohmiya@sci.hokudai.ac.jp
Yokobori
Umi
U
Makida
Yusuke
Y
Sawamura
Masaya
M
D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010755:Organophosphates / Q000737:chemistry*; D013237:Stereoisomerism
D001880:Boranes; D009942:Organometallic Compounds; D010755:Organophosphates; D003300:Copper