Oxidative Olefination of Anilides with Unactivated Alkenes Catalyzed by an (Electron-Deficient η5-Cyclopentadienyl)Rhodium(III) Complex Under Ambient Conditions
The oxidative olefination of sp2 CH bonds of anilides with both activated and unactivated alkenes using an (electron‐deficient η5‐cyclopentadienyl)rhodium(III) complex is reported. In contrast to reactions using this electron‐deficient rhodium(III) catalyst, [Cp*RhCl2]2 showed no activity against o...
Saved in:
Published in | Chemistry : a European journal Vol. 21; no. 25; pp. 9053 - 9056 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
15.06.2015
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | The oxidative olefination of sp2 CH bonds of anilides with both activated and unactivated alkenes using an (electron‐deficient η5‐cyclopentadienyl)rhodium(III) complex is reported. In contrast to reactions using this electron‐deficient rhodium(III) catalyst, [Cp*RhCl2]2 showed no activity against olefination with unactivated alkenes. In addition, the deuterium kinetic isotope effect (DKIE) study revealed that the CH bond cleavage step is thought to be the turnover‐limiting step.
It takes two: It has been established that a dinuclear (electron‐deficient η5‐cyclopentadienyl)RhIII complex is a highly active precatalyst for the oxidative sp2 CH bond olefination of anilides with both activated and unactivated alkenes under ambient conditions (at room temperature under air; see scheme). In contrast, a commonly employed RhIII precatalyst, [{Cp*RhCl2}2], showed no activity against olefination with unactivated alkenes. |
---|---|
Bibliography: | ArticleID:CHEM201501232 Grant-in-Aid for Scientific Research - No. 20675002 istex:6675E3C96D871AA2F09AC677D246C720EAF4D0B0 ark:/67375/WNG-XPZWHB8K-L Ministry of Education, Culture, Sports, Science and Technology ACT-C from Japan Science and Technology Agency (JST, Japan) Umicore KAKEN |
ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201501232 |