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Oxidative Rearrangement Coupling Reaction for the Functionalization of Tetrahydro‐β‐carbolines with Aromatic Amines
Author(s) -
Ye Jinxiang,
Wu Jianlei,
Lv Tingting,
Wu Guolin,
Gao Yu,
Chen Haijun
Publication year - 2017
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.201708893
Subject(s) - surface modification , trifluoroacetic acid , functional group , singlet oxygen , oxidative coupling of methane , chemistry , photochemistry , molecule , oxidative phosphorylation , singlet state , coupling (piping) , combinatorial chemistry , oxygen , organic chemistry , materials science , catalysis , excited state , physics , nuclear physics , polymer , biochemistry , metallurgy
The observation of an unexpected oxidative rearrangement coupling reaction led to the development of a novel method for the efficient functionalization of tetrahydro‐β‐carbolines (THβCs). The treatment of THβCs with photogenerated singlet oxygen ( 1 O 2 ) afforded unstable dioxetanes, which underwent further transformation to form new bonds in the presence of trifluoroacetic acid. This operationally simple protocol exhibits broad functional‐group tolerance and is suitable for the late‐stage functionalization of complex druglike molecules.