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

71 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
Externally publishedYes

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Copper
Phosphates
Borates
Stereochemistry
Alkenes
Functional groups
Olefins

All Science Journal Classification (ASJC) codes

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

Cite this

Copper-catalyzed γ-selective allyl-alkyl coupling between allylic phosphates and alkylboranes. / Ohmiya, Hirohisa; Yokobori, Umi; Makida, Yusuke; Sawamura, Masaya.

In: Journal of the American Chemical Society, Vol. 132, No. 9, 10.03.2010, p. 2895-2897.

Research output: Contribution to journalArticle

Ohmiya, Hirohisa ; Yokobori, Umi ; Makida, Yusuke ; Sawamura, Masaya. / Copper-catalyzed γ-selective allyl-alkyl coupling between allylic phosphates and alkylboranes. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 9. pp. 2895-2897.
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AB - (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.

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