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Rhodium(I)‐Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones
Author(s) -
Sun Tianwen,
Zhang Yuna,
Qiu Bo,
Wang Yafei,
Qin Yuting,
Dong Guangbin,
Xu Tao
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201713179
Subject(s) - benzofuran , rhodium , regioselectivity , aromatization , chemistry , catalysis , combinatorial chemistry , annulation , cascade , cascade reaction , lactone , stereochemistry , organic chemistry , chromatography
Described here is the first example of a rhodium‐catalyzed carboacylation/aromatization cascade of a C=O bond by C−C activation. In this transformation, a reactive rhodaindanone complex is regioselectively generated and adds across a C=O bond with subsequent elimination, thus providing a unique strategy to access a multisubstituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained in good yields. Mechanistic studies show a tricyclic lactone was a viable intermediate. Application of this methodology to the total synthesis of C13‐deOH‐viniferifuran and C13‐deOH‐diptoindonesin G was achieved.