Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes

被引：35

作者：

Bregent, Thibaud ^{[1
]}

Bouillon, Jean-Philippe ^{[1
]}

Poisson, Thomas ^{[1
,2
]}

机构：

[1] Normandie Univ, CNRS, UNIROUEN, INSA Rouen, F-6014 Rouen, France

[2] Inst Univ France, F-75231 Paris, France

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 19期

关键词：

LEWIS-ACID CATALYSIS; PHOTOCHEMICAL-REACTIONS; SELECTIVE ISOMERIZATION; CIS ISOMERIZATION; TRANS; PHOTOISOMERIZATION; COORDINATION; ROUTE;

D O I：

10.1021/acs.orglett.0c02894

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The contra-thermodynamic isomerization of alpha- and beta-substituted cinnamate derivatives catalyzed by the Cu(OAc)(2)/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E -> Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.

引用

页码：7688 / 7693

页数：6

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