A Practical and Catalytic Reductive Olefin Coupling

A redox-economic method for the direct coupling of olefins that uses an inexpensive iron catalyst and a silane reducing agent is reported. Thus, unactivated olefins can be joined directly to electron-deficient olefins in both intra- and intermolecular settings to generate hindered bicyclic systems,...

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Published in:Journal of the American Chemical Society 2014-01, Vol.136 (4), p.1304-1307
Main Authors: Lo, Julian C, Yabe, Yuki, Baran, Phil S
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Catalysts
Communication
Coupling agents
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Iron
Joining
Moisture
Molecular Structure
Olefins
Organic compounds
Oxidation-Reduction
Silanes
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a504t-7ee8e5d63f70718c103b6add50bd334cba326401a4804bd18a9b4718e92781203
cites cdi_FETCH-LOGICAL-a504t-7ee8e5d63f70718c103b6add50bd334cba326401a4804bd18a9b4718e92781203
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container_title Journal of the American Chemical Society
container_volume 136
creator Lo, Julian C
Yabe, Yuki
Baran, Phil S
description A redox-economic method for the direct coupling of olefins that uses an inexpensive iron catalyst and a silane reducing agent is reported. Thus, unactivated olefins can be joined directly to electron-deficient olefins in both intra- and intermolecular settings to generate hindered bicyclic systems, vicinal quaternary centers, and even cyclopropanes in good yield. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. Most importantly, it allows access to many compounds that would be difficult or perhaps impossible to access using other methods.
doi_str_mv 10.1021/ja4117632
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alkenes - chemistry
Catalysis
Catalysts
Communication
Coupling agents
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Iron
Joining
Moisture
Molecular Structure
Olefins
Organic compounds
Oxidation-Reduction
Silanes
Stereoisomerism
title A Practical and Catalytic Reductive Olefin Coupling
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