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Synthesis 2021; 53(11): 1889-1900
DOI: 10.1055/s-0040-1706024
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Photocatalytic Generation of π-Allyltitanium Complexes from Butadiene via a Radical Strategy

Fusheng Li‡
a   Dalian University of Technology, Zhang Dayu School of Chemistry, State Key Laboratory of Fine Chemicals, Dalian, Liaoning 116024, P. R. of China
,
Shuangjie Lin‡
a   Dalian University of Technology, Zhang Dayu School of Chemistry, State Key Laboratory of Fine Chemicals, Dalian, Liaoning 116024, P. R. of China
,
Xiyu Li
a   Dalian University of Technology, Zhang Dayu School of Chemistry, State Key Laboratory of Fine Chemicals, Dalian, Liaoning 116024, P. R. of China
,
Lei Shi  ∗
a   Dalian University of Technology, Zhang Dayu School of Chemistry, State Key Laboratory of Fine Chemicals, Dalian, Liaoning 116024, P. R. of China
b   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. of China
› Author AffiliationsThe project was supported by Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University (No.2020YB03), National College Student Innovation and Entrepreneurship Training Program Support Project, Dalian University of Technology (No. 2020101410101010339), and LiaoNing Revitalization Talents Program (No. XLYC1907126).
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Abstract

The direct conversion of industrial feedstock chemicals into highly valuable fine chemical intermediates is of great appeal to the synthetic community as well as industrial applications. This study reports a conceptually new radical strategy for the photocatalytic generation of π-allyltitanium complexes from butadiene. This novel and environmentally benign strategy enables the direct three-component allylation of carbonyls with 1,3-butadiene and α-bromocarboxylates, providing rapid access to valuable homoallylic alcohols with exceptional regio- and diastereoselectivity control.

Key words

photocatalysis - allylation - radical - butadiene - π-allyl­titanium

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706024.
  • Supporting Information


Publication History

Received: 16 December 2020

Accepted after revision: 15 January 2021

Article published online:
18 February 2021

© 2021. Thieme. All rights reserved

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