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Synthesis of Dibenzo[c,e]oxepin‐5(7 H )‐ones from Benzyl Thioethers and Carboxylic Acids: Rhodium‐Catalyzed Double CH Activation Controlled by Different Directing Groups
Author(s) -
Zhang XiSha,
Zhang YunFei,
Li ZhaoWei,
Luo FeiXian,
Shi ZhangJie
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500486
Subject(s) - rhodium , chemistry , catalysis , aryl , molecule , oxidative coupling of methane , stereochemistry , double bond , selectivity , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross‐oxidative coupling.