Trimerization of enones under air enabled by NHC/NaO: T Bu via a SET radical pathway

Yuexia Zhang; Xingxing Wu; Lin Hao; Zeng Rong Wong; Sherman J.L. Lauw; Song Yang; Richard D. Webster; Yonggui Robin Chi

doi:10.1039/c6qo00738d

Trimerization of enones under air enabled by NHC/NaO: T Bu via a SET radical pathway

Yuexia Zhang, Xingxing Wu, Lin Hao, Zeng Rong Wong, Sherman J.L. Lauw, Song Yang, Richard D. Webster^*, Yonggui Robin Chi

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	467-471
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	4
Issue number	3
DOIs	https://doi.org/10.1039/c6qo00738d
Publication status	Published - Mar 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 the Partner Organisations.

ASJC Scopus Subject Areas

Organic Chemistry

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title = "Trimerization of enones under air enabled by NHC/NaO: T Bu via a SET radical pathway",

abstract = "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.",

author = "Yuexia Zhang and Xingxing Wu and Lin Hao and Wong, {Zeng Rong} and Lauw, {Sherman J.L.} and Song Yang and Webster, {Richard D.} and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2017 the Partner Organisations.",

year = "2017",

month = mar,

doi = "10.1039/c6qo00738d",

language = "English",

volume = "4",

pages = "467--471",

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T1 - Trimerization of enones under air enabled by NHC/NaO

T2 - T Bu via a SET radical pathway

AU - Zhang, Yuexia

AU - Wu, Xingxing

AU - Hao, Lin

AU - Wong, Zeng Rong

AU - Lauw, Sherman J.L.

AU - Yang, Song

AU - Webster, Richard D.

AU - Chi, Yonggui Robin

PY - 2017/3

Y1 - 2017/3

N2 - 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.

AB - 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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DO - 10.1039/c6qo00738d

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JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

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ER -

Trimerization of enones under air enabled by NHC/NaO: T Bu via a SET radical pathway

Abstract

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