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Photocatalytic Aerobic Oxidative Ring Expansion of Cyclic Ketones to Macrolactones by Cerium and Cyanoanthracene Catalysis
Author(s) -
Du Jianbo,
Yang Xiaokun,
Wang Xin,
An Qing,
He Xu,
Pan Hui,
Zuo Zhiwei
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012720
Subject(s) - cerium , photocatalysis , catalysis , ring (chemistry) , materials science , visible spectrum , oxidative phosphorylation , photochemistry , chemistry , combinatorial chemistry , nanotechnology , optoelectronics , inorganic chemistry , organic chemistry , biochemistry
We describe a cerium‐catalyzed aerobic oxidative ring expansion for the expedient construction of synthetically challenging macrolactones under visible‐light conditions. Cyanoanthracene has been employed as co‐catalyst to accelerate the turnover of the cerium cycle leading to a fast conversion within 20 min of irradiation. Taking advantage of the high efficiency and operationally simple conditions, a collection of over 100 macrolactones equipped with ring systems ranging from 9‐ to 19‐membered macrocycles have been prepared from simple building blocks. Moreover, the enabling potential of this strategy to simplify the generation of molecular complexity has been demonstrated through the concise synthesis of sonnerlactone.