Conjugate Addition of Perfluoroarenes to α,β-Unsaturated Carbonyls Enabled by an Alkoxide-Hydrosilane System: Implication of a Radical Pathway

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Title
Conjugate Addition of Perfluoroarenes to α,β-Unsaturated Carbonyls Enabled by an Alkoxide-Hydrosilane System: Implication of a Radical Pathway
Author(s)
Weilong Xie; Sung-Woo Park; Hoimin Jung; Dongwook Kim; Mu-Hyun Baik; Sukbok Chang
Publication Date
2018-08
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.140, no.30, pp.9659 - 9668
Publisher
AMER CHEMICAL SOC
Abstract
Conjugate addition of organometallic reagents to α,β-unsaturated carbonyls is a key strategy for the construction of carbon-carbon bond in organic synthesis. Although direct C-H addition to unsaturated bonds via transition metal catalysis is explored in recent years, electron-deficient arenes that do not bear directing groups continue to be challenging. Herein we disclose the first example of a conjugate addition of perfluoroarenes to α,β-unsaturated carbonyls enabled by an alkoxide-hydrosilane system. The reaction is convenient to carry out at room temperature over a broad range of substrates and reactants to furnish synthetically versatile products in high to excellent yields. Mechanistic experiments in combination with computational studies suggest that a radical pathway is most likely operative in this transformation. The hypervalent silicate and silanide species, which are relevant to the proposed mechanism, were observed experimentally by NMR and single crystal X-ray diffraction analyses. Copyright © 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/4940
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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