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基于电子给体-受体复合物的可见光驱动的烷基苯胺与二苯甲酰基乙烯的立体选择性环化反应

Visible-Light-Driven Stereoselective Annulation of Alkyl Anilines and Dibenzoylethylenes via Electron Donor-Acceptor Complexes.

作者信息

Runemark August, Zacharias Savannah C, Sundén Henrik

机构信息

Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Kemivägen 10, 41296 Gothenburg, Sweden.

Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, 41296 Gothenburg, Sweden.

出版信息

J Org Chem. 2021 Jan 15;86(2):1901-1910. doi: 10.1021/acs.joc.0c02819. Epub 2021 Jan 4.

Abstract

A catalyst-free, stereoselective visible-light-driven annulation reaction between alkenes and ,-substituted dialkyl anilines for the synthesis of substituted tetrahydroquinolines is presented. The reaction is driven by the photoexcitation of an electron donor-acceptor (EDA) complex, and the resulting products are obtained in good to high yields with complete diastereoselectivity. Mechanistic rationale and photochemical characterization of the EDA-complex are provided.

摘要

本文报道了一种无催化剂、立体选择性可见光驱动的烯烃与α,β-二取代二烷基苯胺之间的环化反应,用于合成取代的四氢喹啉。该反应由电子供体-受体(EDA)络合物的光激发驱动,所得产物以良好至高收率获得,且具有完全的非对映选择性。文中还提供了EDA络合物的机理原理和光化学表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d9c/7884011/22a3afac1527/jo0c02819_0002.jpg

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