Diverse Visible-Light-Promoted Functionalizations of Benzotriazoles Inspired by Mechanism-Based Luminescence Screening

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• 作者：Michael Teders ; Dr. Adri&aacute ; n Gó ; mez-Su&aacute ; rez ; Lena Pitzer ; Prof. Dr. Matthew N. Hopkinson and Prof. Dr. Frank Glorius
• 刊名：Angewandte Chemie International Edition
• 出版年：2017
• 出版时间：January 16, 2017
• 年：2017
• 卷：56
• 期：3
• 页码：902-906
• 全文大小：1828K
• ISSN：1521-3773

文摘

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.