Synthesis of unsymmetrical diarylethynes by Pd(0)/Cu(I)-cocatalyzed Sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl tosylates or mesylates

Yasushi Nishihara; Daisuke Ogawa; Shintaro Noyori; Masayuki Iwasaki

doi:10.1246/cl.2012.1503

Synthesis of unsymmetrical diarylethynes by Pd(0)/Cu(I)-cocatalyzed Sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl tosylates or mesylates

Yasushi Nishihara, Daisuke Ogawa, Shintaro Noyori, Masayuki Iwasaki

Research Institute for Interdisciplinary Science

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

14 Citations (Scopus)

Abstract

Palladium/copper-cocatalyzed cross-coupling reactions of alkynylsilanes with aryl tosylates or mesylates afforded the corresponding unsymmetrical diarylethynes in moderate to good yields. The optimized reaction conditions to afford higher yields of cross-coupled products were found to be 5mol% of [PdCl ₂(bpy)], 15 mol% of BrettPhos, and 10 mol% of Cu ¹Cl in DMF as a solvent.

Original language	English
Pages (from-to)	1503-1505
Number of pages	3
Journal	Chemistry Letters
Volume	41
Issue number	11
DOIs	https://doi.org/10.1246/cl.2012.1503
Publication status	Published - Nov 28 2012

ASJC Scopus subject areas

Chemistry(all)

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author = "Yasushi Nishihara and Daisuke Ogawa and Shintaro Noyori and Masayuki Iwasaki",

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AU - Nishihara, Yasushi

AU - Ogawa, Daisuke

AU - Noyori, Shintaro

AU - Iwasaki, Masayuki

PY - 2012/11/28

Y1 - 2012/11/28

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AB - Palladium/copper-cocatalyzed cross-coupling reactions of alkynylsilanes with aryl tosylates or mesylates afforded the corresponding unsymmetrical diarylethynes in moderate to good yields. The optimized reaction conditions to afford higher yields of cross-coupled products were found to be 5mol% of [PdCl 2(bpy)], 15 mol% of BrettPhos, and 10 mol% of Cu 1Cl in DMF as a solvent.

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Synthesis of unsymmetrical diarylethynes by Pd(0)/Cu(I)-cocatalyzed Sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl tosylates or mesylates

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