Visible Light‐Mediated Construction of Sulfonated Dibenzazepines

• Published in: Chinese journal of chemistry Vol. 39; no. 8; pp. 2220 - 2226
• Main Authors: Qu, Chuan‐Hua, Song, Gui‐Ting, Ou, Jian‐Hua, Tang, Dian‐Yong, Xu, Zhi‐Gang, Chen, Zhong‐Zhu
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 01.08.2021; Wiley; Wiley Subscription Services, Inc
• Subjects: Alkynes; Annulation; Catalysis; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Photocatalysis; Photoredox catalysis; Physical Sciences; Radical reactions; Science & Technology; Substrates; Sulfonated dibenzazepines; Ugi reaction; Ugi reaction; Photocatalysis; SULFONYLATION; CASCADE; Sulfonated dibenzazepines; ALKENES; DIENES; FACILE SYNTHESIS; Radical reactions; CHLORIDES; Annulation; DERIVATIVES; RADICAL-ADDITION-REACTIONS; CYCLIZATION
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202100194

Main observation and conclusion A new method to access sulfonated dibenz[b,e]azepines via visible‐light photoredox catalysis is described. Employing inexpensive and commercially available sulfonyl chlorides to form the sulfonyl radicals enables the alkyne addition reaction followed by a 7‐membered radical cyclization step to furnish sulfonated dibenzazepines. In addition, an Ugi‐type multicomponent reaction (MCR) for the synthesis of o‐aminophenylacetylene derivatives can also be used as a rapid substrate synthesis method for the cascade radical cyclization protocol to obtain a series of highly functionalized sulfonylated dibenzazepines, which undoubtedly greatly simplifies the synthetic steps of the dibenzazepine compounds that are important core structures in pharmaceuticals. Highly functionalized sulfonated dibenzazepines were rapidly assembled using Ugi products and commercially accessible sulfonyl chlorides in one step via photoredox.