Rh(III)-Catalyzed Enone Carbonyl/Ketone-Directed Aerobic C-H Olefination of Aromatics with Unactivated Olefins

被引：11

作者：

Jeganmohan, Masilamani ^{[1
]}

Shambhavi, Chikkabagilu Nagaraju ^{[1
]}

机构：

[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, Tamil Nadu, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期

关键词：

SELECTIVE OLEFINATION; BOND; ACTIVATION; ALKENES; ALKENYLATION; ARENES; HETEROAROMATICS; ALLYLATION; ANILIDES; INDOLES;

D O I：

10.1021/acs.joc.2c01730

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(III)-catalyzed weak enone carbonyl/ketoneassisted aerobic oxidative C-H olefination of aromatics with unactivated alkenes has been developed. This protocol involves cross-dehydrogenative Heck-type olefination reaction of various substituted biologically relevant chalcones and aromatic ketones such as acetophenones and chromones with various functionalized unactivated olefins in moderate to good yields. Further, ortho- alkylation of chalcones with norbornene is also demonstrated. A possible reaction mechanism involving weak chelation-assisted C- H activation/insertion/beta-hydride elimination was proposed and supported by the deuterium labeling studies.

引用

页码：13236 / 13258

页数：23

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