Controllable Isomerization of Alkenes by Dual Visible‐Light‐Cobalt Catalysis

We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controll...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-04, Vol.58 (17), p.5723-5728
Main Authors: Meng, Qing‐Yuan, Schirmer, Tobias E., Katou, Kousuke, König, Burkhard
Format: Article
Language:English
Subjects:
alkene isomerization
Alkenes
Catalysis
Cobalt
Communication
Communications
Isomerization
Isomers
Ligands
photosynthesis
Stability
visible light catalysis
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Summary:We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization. A mild and highly efficient translocation of alkenes by dual visible‐light‐cobalt catalysis has been developed. By the proper choice of ligands, isomerization over one position or more than one position with tolerance of a variety of functional groups can be selectively achieved.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201900849