Trimerization of enones under air enabled by NHC/NaOtBu via a SET radical pathway

Trimerization of enones under air enabled by NHC/NaOtBu via a SET radical pathway

An unusual trimerization of enone via a formal [2 + 2 + 2] process is disclosed. The reaction is initiated by a radical process enabled by NaOtBu and N-heterocyclic carbene (NHC). Molecular oxygen (air) is involved in key steps of the radical intermediate formation and carbon–carbon bond cleavage in...

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Bibliographic Details
Main Authors: Zhang, Yuexia, Wu, Xingxing, Hao, Lin, Wong, Zeng Rong, Lauw, Sherman Jun Liang, Yang, Song, Webster, Richard David, Chi, Yonggui Robin
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2017
Subjects:
Trimerization
Radical intermediates
Online Access:https://hdl.handle.net/10356/81973
http://hdl.handle.net/10220/42449
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Institution: Nanyang Technological University
Language: English
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Summary:An unusual trimerization of enone via a formal [2 + 2 + 2] process is disclosed. The reaction is initiated by a radical process enabled by NaOtBu and N-heterocyclic carbene (NHC). Molecular oxygen (air) is involved in key steps of the radical intermediate formation and carbon–carbon bond cleavage in this trimerization reaction to form highly substituted cyclohexane derivatives. In previous studies, alkali metal tert-butoxides such as NaOtBu were mainly employed to generate radical intermediates from aryl halides. Here we provide a new avenue in using NaOtBu and combined NHC/NaOtBu to generate radical intermediates from enones for further reactions.

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