Carbonyl Olefin Metathesis and Dehydrogenative Cyclization of Aromatic Ketones and gem‐Difluoroalkenes

Author:

Zhang Yunxiao12,Wang Jiaxin12,Guo Youyuan12,Liu Shanshan12,Shen Xiao12ORCID

Affiliation:

1. The Institute for Advanced Studies Engineering Research Center of Organosilicon Compounds & Materials Ministry of Education Wuhan University 299 Bayi Road Wuhan Hubei 430072 China

2. Shenzhen Research Institute of Wuhan University Shenzhen 518057 China

Abstract

AbstractThe beauty of one‐pot cascade reaction lies in the efficient disconnection and construction of several bonds in a single reaction flask, without the isolation of any intermediates. Herein, we report the first photoinduced thermally promoted cascade reactions of readily available aromatic ketones and aromatic gem‐difluoroalkenes for the synthesis of phenanthrenes which possess potential utility in drug design and materials science. The reaction combines carbonyl‐olefin metathesis (cascade photoinduced [2+2] cyclization and thermally controlled retro [2+2] cyclization) and dehydrogenative cyclization (cascade photoinduced conrotatory 6π electrocyclization and collidine‐promoted dehydrogenative aromatization) together in one pot. The oxidant‐free, acid‐free and metal‐free reaction shows broad substrate scope and wide functional group tolerance.

Funder

National Key Research and Development Program of China

Basic and Applied Basic Research Foundation of Guangdong Province

Fundamental Research Funds for Central Universities of the Central South University

Publisher

Wiley

Subject

General Medicine

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