Trimerization of enones under air enabled by NHC/NaOtBu via a SET radical pathway
Wong, Zeng Rong
Lauw, Sherman Jun Liang
Webster, Richard David
Chi, Yonggui Robin
Date of Issue2016
School of Physical and Mathematical Sciences
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.
Organic Chemistry Frontiers
© 2016 the Partner Organisations (The Chinese Chemical Society, Shanghai Institute of Organic Chemistry, and Royal Society of Chemistry). This is the author created version of a work that has been peer reviewed and accepted for publication by Organic Chemistry Frontiers, published by Royal Society of Chemistry on behalf of the Partner Organisations. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [http://dx.doi.org/10.1039/C6QO00738D].