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Diverse Visible‐Light‐Promoted Functionalizations of Benzotriazoles Inspired by Mechanism‐Based Luminescence Screening
Author(s) -
Teders Michael,
GómezSuárez Adrián,
Pitzer Lena,
Hopkinson Matthew N.,
Glorius Frank
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.201609393
Subject(s) - borylation , chemistry , aniline , combinatorial chemistry , luminescence , photochemistry , photocatalysis , reaction mechanism , mechanism (biology) , organic chemistry , materials science , catalysis , aryl , optoelectronics , alkyl , philosophy , epistemology
Three new visible‐light‐promoted functionalizations of benzotriazole substrates were discovered using a mechanism‐based screening method. ortho ‐Thiolated, borylated, and alkylated N ‐arylbenzamide products were obtained under mild reaction conditions in a new denitrogenative synthetic approach to functionalized aniline derivatives. The functional group tolerance of the borylation reaction was further analyzed in the first application of an additive‐based robustness screen in a photocatalytic transformation. All the functionalizations proceed via photocatalytically initiated chain mechanisms as indicated by determination of the reaction quantum yields and Stern–Volmer analyses.