Affiliation:
1. Frontiers Science Center for Transformative Molecules Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Chemistry and Chemical Engineering and Zhangjiang Institute for Advanced Study Shanghai Jiao Tong University Shanghai 200240 P. R. China
2. Department of Chemistry and Biochemistry Oberlin College 119 Woodland St. Oberlin Ohio 44074 USA
Abstract
Abstract(Hetero)arene reduction is one of the key avenues for synthesizing related cyclic alkenes and alkanes. While catalytic hydrogenation and Birch reduction are the two broadly utilized approaches for (hetero)arene reduction across academia and industry over the last century, both methods have encountered significant chemoselectivity challenges. We hereby introduce a highly chemoselective quinoline and isoquinoline reduction protocol operating through selective energy transfer (EnT) catalysis, which enables subsequent hydrogen atom transfer (HAT). The design of this protocol bypasses the conventional metric of reduction reaction, that is, the reductive potential, and instead relies on the triplet energies of the chemical moieties and the kinetic barriers of energy and hydrogen atom transfer events. Many reducing labile functional groups, which were incompatible with previous (hetero)arene reduction reactions, are retained in this reaction. We anticipate that this protocol will trigger the further advancement of chemoselective arene reduction and enable the current arene‐rich drug space to escape from flatland.
Funder
National Natural Science Foundation of China
Fundamental Research Funds for the Central Universities
Natural Science Foundation of Shanghai Municipality
Subject
General Chemistry,Catalysis
Cited by
6 articles.
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