Regioselective hydration of terminal alkynes catalyzed by a neutral gold(I) complex [(IPr)AuCl] and one-pot synthesis of optically active secondary alcohols from terminal alkynes by the combination of [(IPr)AuCl] and Cp*RhCl[(R,R)-TsDPEN

The Journal of Organic Chemistry
Feng LiGuangjun Zhu

Abstract

A neutral gold(I) complex [(IPr)AuCl] (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene) was found to be a highly effective catalyst for the hydration of terminal alkynes, including aromatic alkynes and aliphatic alkynes. The desired methyl ketones were obtained in high yields with complete regioselectivities. Furthermore, a series of optically active secondary alcohols could be obtained in high yield with good to excellent enatioselectivities via one-pot sequential hydration/asymmetric transfer hydrogenation (ATH) from terminal alkynes by the combination of of [(IPr)AuCl] and Cp*RhCl[(R,R)-TsDPEN] (Cp* = pentamethylcyclopentadienyl, TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine). Notably, this research exhibited the potential of the direct use of neutral gold(I) complexes instead of cationic ones as catalysts for the activation of multiple bonds for organic synthesis.

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Citations

Mar 10, 2016·Journal of the American Chemical Society·Patricia García-Domínguez, Cristina Nevado
Oct 2, 2015·Journal of the American Chemical Society·Jie LuMarcus Weck
Dec 23, 2016·The Journal of Organic Chemistry·Tingjie YouYuanzhi Xia
Jun 10, 2015·Organic & Biomolecular Chemistry·Beatrice RanieriAntonio M Echavarren
Jun 15, 2017·Chemical Communications : Chem Comm·Shengtai HouYun Li
Nov 9, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Els De CanckPascal Van Der Voort
Feb 11, 2020·Chemical Communications : Chem Comm·Zhaoyang ChengZhan Lu
Mar 12, 2019·ChemCatChem·Anne C H JansJoost N H Reek
Aug 10, 2021·The Journal of Organic Chemistry·Yu-Ming YangZhuangzhu Luo
Apr 13, 2018·The Journal of Organic Chemistry·Luiz F T NovaesJulio C Pastre

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