Palladium-free synthesis of unsymmetrical diarylethynes by cross-coupling reaction of alkynylboronates with aryl iodides catalyzed by CuCl

Daisuke Ogawa; Jing Li; Masato Suetsugu; Jiao Jiao; Masayuki Iwasaki; Yasushi Nishihara

doi:10.1016/j.tetlet.2012.11.069

Palladium-free synthesis of unsymmetrical diarylethynes by cross-coupling reaction of alkynylboronates with aryl iodides catalyzed by CuCl

Daisuke Ogawa, Jing Li, Masato Suetsugu, Jiao Jiao, Masayuki Iwasaki, Yasushi Nishihara

Research Institute for Interdisciplinary Science

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

11 Citations (Scopus)

Abstract

A series of unsymmetrical diarylethynes have been synthesized by the copper-catalyzed cross-coupling reaction of alkynylboronates with aryl iodides in high to excellent yields under palladium-free conditions. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible with this reaction.

Original language	English
Pages (from-to)	518-521
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2012.11.069
Publication status	Published - Feb 6 2013

Keywords

Alkynylboronates
Copper
Sonogashira-Hagihara coupling
Stephens-Castro reaction
Suzuki-Miyaura coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Palladium-free synthesis of unsymmetrical diarylethynes by cross-coupling reaction of alkynylboronates with aryl iodides catalyzed by CuCl",

abstract = "A series of unsymmetrical diarylethynes have been synthesized by the copper-catalyzed cross-coupling reaction of alkynylboronates with aryl iodides in high to excellent yields under palladium-free conditions. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible with this reaction.",

keywords = "Alkynylboronates, Copper, Sonogashira-Hagihara coupling, Stephens-Castro reaction, Suzuki-Miyaura coupling",

author = "Daisuke Ogawa and Jing Li and Masato Suetsugu and Jiao Jiao and Masayuki Iwasaki and Yasushi Nishihara",

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T1 - Palladium-free synthesis of unsymmetrical diarylethynes by cross-coupling reaction of alkynylboronates with aryl iodides catalyzed by CuCl

AU - Ogawa, Daisuke

AU - Li, Jing

AU - Suetsugu, Masato

AU - Jiao, Jiao

AU - Iwasaki, Masayuki

AU - Nishihara, Yasushi

PY - 2013/2/6

Y1 - 2013/2/6

N2 - A series of unsymmetrical diarylethynes have been synthesized by the copper-catalyzed cross-coupling reaction of alkynylboronates with aryl iodides in high to excellent yields under palladium-free conditions. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible with this reaction.

AB - A series of unsymmetrical diarylethynes have been synthesized by the copper-catalyzed cross-coupling reaction of alkynylboronates with aryl iodides in high to excellent yields under palladium-free conditions. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible with this reaction.

KW - Alkynylboronates

KW - Copper

KW - Sonogashira-Hagihara coupling

KW - Stephens-Castro reaction

KW - Suzuki-Miyaura coupling

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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