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配体控制的铱催化炔烃与乙醇的半氢化反应:E-和 Z-烯烃的高立体选择性合成。

Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes.

机构信息

Medical School, Institute of Reproductive Medicine, Nantong University, Nantong 226019, China.

出版信息

Chem Commun (Camb). 2019 Feb 7;55(13):1903-1906. doi: 10.1039/c8cc09714c.

DOI:10.1039/c8cc09714c
PMID:30675609
Abstract

A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4'-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.

摘要

发展了一种在手性铱配合物催化下,以乙醇为氢源对炔烃进行顺式选择性半氢化的方法。通过配体调控实现了有效的选择性控制。1,2-双(二苯基膦)乙烷(DPPE)和 1,5-环辛二烯(COD)的使用对于炔烃的立体选择性半氢化至关重要。该方法的通用性通过合成 40 多种具有良好立体选择性的烯烃得到了突出体现。我们还通过研究松柏素和 4,4'-二羟基二苯乙烯(DHS)对斑马鱼的影响,研究了该方法在实际应用中的价值,斑马鱼是一种脊椎动物模型。

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