Copper-catalyzed γ-selective allyl-alkyl coupling between allylic phosphates and alkylboranes

Hirohisa Ohmiya, Umi Yokobori, Yusuke Makida, Masaya Sawamura

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

(Figure Presented) Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete γ- 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.

Original languageEnglish
Pages (from-to)2895-2897
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number9
DOIs
Publication statusPublished - Mar 10 2010

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Copper-catalyzed γ-selective allyl-alkyl coupling between allylic phosphates and alkylboranes'. Together they form a unique fingerprint.

  • Cite this