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醛的光氧化还原炔丙基化反应中钛的催化作用

Photoredox Propargylation of Aldehydes Catalytic in Titanium.

作者信息

Calogero Francesco, Gualandi Andrea, Matteo Marco Di, Potenti Simone, Fermi Andrea, Bergamini Giacomo, Cozzi Pier Giorgio

机构信息

Alma Mater Studiorum, Università di Bologna, Dipartimento di Chimica "G. Ciamician", Via Selmi 2, 40126 Bologna, Italy.

Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy.

出版信息

J Org Chem. 2021 May 7;86(9):7002-7009. doi: 10.1021/acs.joc.1c00521. Epub 2021 Apr 22.

Abstract

A practical and effective photoredox propargylation of aldehydes promoted by 10 mol % of [CpTiCl] is presented. No stoichiometric metals or scavengers are used for the process. A catalytic amount of the cheap and simply prepared organic dye 3DPAFIPN is used as the reductant for titanium. The reaction displayed a broad scope, and no traces of allenyl isomers were detected for simple propargyl bromide, whereas mixtures of propargyl and allenyl isomers were observed for substituted propargyl bromides.

摘要

本文介绍了一种由10 mol%的[CpTiCl]促进的实用且有效的醛的光氧化还原炔丙基化反应。该过程不使用化学计量的金属或清除剂。使用催化量的廉价且易于制备的有机染料3DPAFIPN作为钛的还原剂。该反应适用范围广泛,对于简单的炔丙基溴未检测到丙二烯异构体的痕迹,而对于取代的炔丙基溴则观察到炔丙基异构体和丙二烯异构体的混合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b7d0/8279488/f140355dbcf0/jo1c00521_0002.jpg

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