Photoexcited cobalt catalysed endo -selective alkyl Heck reaction

Herein, we report an intramolecular -selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols. The reaction leads to the formation of seven- and eight-membered siloxycycles in excellent yields, which could be further converted into the corresponding allylic alcohols upon oxidation....

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-03, Vol.59 (26), p.3862-3865
Main Authors: Wang, Chenyang, Azofra, Luis Miguel, Dam, Phong, Espinoza-Suarez, Edelman J, Do, Hieu Trung, Rabeah, Jabor, Brückner, Angelika, El-Sepelgy, Osama
Format: Article
Language:English
Subjects:
Alcohols
Atomic energy levels
Ethers
Oxidation
Phenols
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Summary:Herein, we report an intramolecular -selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols. The reaction leads to the formation of seven- and eight-membered siloxycycles in excellent yields, which could be further converted into the corresponding allylic alcohols upon oxidation. Thus, this method could be used for the selective ( )-hydroxymethylation of -hydroxystyrenes and alkenols. Rapid scan EPR experiments and DFT calculations suggest a concerted -hydrogen elimination event to take place in the triplet state.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc06967a