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

Jiao Jiao; Kiyohiko Nakajima; Yasushi Nishihara

doi:10.1021/ol401333j

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

Jiao Jiao, Kiyohiko Nakajima, Yasushi Nishihara

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

Abstract

A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe₂Si-B_pin 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 language	English
Pages (from-to)	3294-3297
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	13
DOIs	https://doi.org/10.1021/ol401333j
Publication status	Published - Jul 5 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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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year = "2013",

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doi = "10.1021/ol401333j",

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T1 - Synthesis of multisubstituted olefins through regio- and stereoselective silylborylation of an alkynylboronate/chemoselective cross-coupling sequences

AU - Jiao, Jiao

AU - Nakajima, Kiyohiko

AU - Nishihara, Yasushi

PY - 2013/7/5

Y1 - 2013/7/5

N2 - 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.

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

Abstract

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