Synthesis of multisubstituted olefins through regio- and stereoselective silylborylation of an alkynylboronate/chemoselective cross-coupling sequences

Jiao Jiao, Kiyohiko Nakajima, Yasushi Nishihara

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-Bpin undergoes a Pd(OAc) 2/tOctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (Z)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.

Original languageEnglish
Pages (from-to)3294-3297
Number of pages4
JournalOrganic Letters
Volume15
Issue number13
DOIs
Publication statusPublished - Jul 5 2013

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Regioselectivity
cross coupling
Alkenes
alkenes
Derivatives
synthesis
products
palladium(II) acetate

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of multisubstituted olefins through regio- and stereoselective silylborylation of an alkynylboronate/chemoselective cross-coupling sequences. / Jiao, Jiao; Nakajima, Kiyohiko; Nishihara, Yasushi.

In: Organic Letters, Vol. 15, No. 13, 05.07.2013, p. 3294-3297.

Research output: Contribution to journalArticle

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abstract = "A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-Bpin undergoes a Pd(OAc) 2/tOctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (Z)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.",
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AB - A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-Bpin undergoes a Pd(OAc) 2/tOctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (Z)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.

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