Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis

Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation u...

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Veröffentlicht in:Organic letters 2023-07, Vol.25 (27), p.5094-5099
Hauptverfasser: Hao, Erjun, Lu, Binghui, Liu, Yonghong, Yang, Tianxiao, Yan, Huaipu, Ding, Xiaobo, Jin, Yunhe, Shi, Lei
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Sprache:eng
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Zusammenfassung:Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation using 1,3-butadiene as an allyl group source under visible light conditions. This sustainable and straightforward method has facilitated the rapid production of diverse allylic 1,3-thioalcohols with exceptional regio- and diastereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01822