Diverse Visible‐Light‐Promoted Functionalizations of Benzotriazoles Inspired by Mechanism‐Based Luminescence Screening. Issue 3 (21st December 2016)

• Record Type: Journal Article
• Authors: Teders, Michael; Gómez‐Suárez, Adrián; Pitzer, Lena; Hopkinson, Matthew N.; Glorius, Frank
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 3(2017)
• Page Start: 902
• Page End: 906
• Publication Date: 2016-12-21
• Subjects: benzotriazoles -- luminescence -- photocatalysis -- radicals -- screening; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201609393
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Trinity ! Three visible‐light‐promoted functionalization reactions of benzotriazole substrates were discovered using a mechanism‐based screening method and provided ortho ‐thiolated, ‐borylated, and ‐alkylated N ‐arylbenzamide products. The functional group tolerance of the borylation reaction was further analyzed by the first application of an additive‐based robustness screen in a photocatalytic transformation.