Diverse Visible‐Light‐Promoted Functionalizations of Benzotriazoles Inspired by Mechanism‐Based Luminescence Screening | Zendy

Teders Michael | Zendy; GómezSuárez Adrián | Zendy; Pitzer Lena | Zendy; Hopkinson Matthew N. | Zendy; Glorius Frank | Zendy

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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.

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