Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides,Journal of the American Chemical Society

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Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-11-13 , DOI: 10.1021/jacs.8b10874
Chunlin Tang ₁ , Ran Zhang ₁ , Bo Zhu ₁ , Junkai Fu _{1,

2} , Yi Deng ₁ , Li Tian ₁ , Wei Guan ₁ , Xihe Bi ₁

Affiliation

A new type of intermolecular alkylative olefination of unactivated olefins and alkyl halides has been realized for the first time. This copper-promoted Heck-type reaction employs a directing-group strategy to efficiently produce the coupled alkyl olefin products with excellent regio- and stereoselectivity. A broad substrate scope including 1°, 2°, and 3° alkyl bromides and various nonactivated alkenes could be well tolerated. DFT calculations disclosed a dimethyl sulfoxide assisted concerted H-Br elimination process of a conformationally strained Cu(III) cyclic transition state.

中文翻译：

未活化烯烃和烷基卤化物的定向铜催化分子间 Heck 型反应

首次实现了未活化烯烃和卤代烷的新型分子间烷基化烯化。这种铜促进的 Heck 型反应采用定向基团策略有效地生产具有优异区域和立体选择性的偶联烷基烯烃产物。可以很好地耐受广泛的底物范围，包括 1°、2° 和 3° 烷基溴化物和各种未活化的烯烃。DFT 计算揭示了二甲基亚砜辅助协调 H-Br 消除构象应变 Cu(III) 环状过渡态的过程。

更新日期：2018-11-13

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