A stereoselective palladium-mediated reductive coupling of electron-deficient terminal iodoalkenes

被引：13

作者：

Batsanov, Andrei S. ^{[1
]}

Knowles, Jonathan P. ^{[1
]}

Samsam, Benedict ^{[1
]}

Whiting, Andrew ^{[1
]}

机构：

[1] Univ Durham, Dept Chem, Durham DH1 3LE, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 02期

关键词：

alkenes; C-C coupling; electron-deficient compounds; palladium; reduction; stereoselectivity;

D O I：

10.1002/adsc.200700464

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Iodoacrylate esters undergo palladium-catalysed reductive homocoupling to derive dienyl diester derivatives. This reductive coupling can be extended to ester-substituted terminal iododienes to derive tetraene diesters. In all cases, the reactions show relatively high levels of stereocontrol, which shows an inversion of stereochemistry about one iodoalkene unit. This process, and the suggestion that the reaction releases diiodine, is consistent with a syn-1,2-addition of an iodopalladium(II)-alkene species across another iodoalkene unit (carbometallation step), followed by reductive syn-elimination of iodopalladium iodide to derive palladium(II) iodide. It appears that under the reaction conditions employed, palladium(II) iodide may equilibrate to palladium(0) and diiodine, which can be observed or trapped out from the reaction mixture.

引用

页码：227 / 233

页数：7

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