Diastereoselective 1,2-difunctionalization of 1,3-enynes enabled by merging photoexcited Hantzsch ester with chromium catalysis

文献情報

出版日 2023-10-20

DOI 10.1039/D3QO01522J

インパクトファクター 5.281

著者

Jia Wu, Xiangyun Xu, Chongwen Duan, Shan Chen, Dan Wang, Likui Fang, Weiyang Tang, Fusheng Li

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要旨

1,3-Enynes have been widely recognized as prevalent synthons for the construction of valuable allenes, 1,3-dienes, and propargylic derivatives. However, significant advancements have primarily focused on elucidating the ionic reaction mechanism. The selective difunctionalization of 1,3-enynes involving radicals remains an outstanding challenge in particular within the realm of radical 1,2-difunctionalization. Herein, we present a comprehensive account of the regio- and diastereoselective radical multicomponent 1,2-dialkylation of 1,3-enynes via photoexcited Hantzsch ester and chromium co-catalysis to furnish highly valuable homopropargylic alcohols. Our protocol shows excellent compatibility and 1,2-regioselectivity. Remarkably, this innovative approach obviates the need for external photocatalysts, stoichiometric metal reductants, or additional additives, offering a novel strategy for the valuable transformation of 1,3-enynes.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Diastereoselective 1,2-difunctionalization of 1,3-enynes enabled by merging photoexcited Hantzsch ester with chromium catalysis

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