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Tandem Organocatalysis and Photocatalysis: An Anthraquinone‐Catalyzed Indole‐C3‐Alkylation/Photooxidation/1,2‐Shift Sequence
Author(s) -
Lerch Stephanie,
Unkel LisaNatascha,
Brasholz Malte
Publication year - 2014
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.201402920
Subject(s) - indoline , anthraquinone , indole test , chemistry , tandem , catalysis , photocatalysis , alkylation , photochemistry , organocatalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis , materials science , composite material
Quinones exhibit orthogonal ground‐ and excited‐state reactivities and are therefore highly suitable organocatalysts for the development of sequential catalytic processes. Herein, the discovery of an anthraquinone‐catalyzed thermal indole‐C3‐alkylation with benzylamines is described, which can be combined sequentially with a new visible‐light‐driven catalytic photooxidation/1,2‐shift reaction. The one‐flask tandem process converts indoles into 3‐benzylindole intermediates, which are further transformed into new fluorescent 2,2‐disubstituted indoline‐3‐one derivatives.