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4-Aminobenzotriazole (ABTA) as a Removable Directing Group for Palladium-Catalyzed Aerobic Oxidative C-H Olefination.

ABSTRACT: 4-Aminobenzotriazole (ABTA) was applied as an effective removable directing group (DG) in Pd-catalyzed C-H activation for the first time. Compared with the widely applied pyridine and quinoline analogs, ABTA showed significantly improved reactivity, achieving aerobic oxidative C-H olefination in excellent yields (up to 95% vs <50% with other reported DGs under identical conditions). Using this new strategy, macrocyclization was achieved to give cyclic peptides in good yields with easy ABTA removal under mild conditions, highlighting the promising potential of this new DG.

SUBMITTER: Wang Z

PROVIDER: S-EPMC10264207 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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4-Aminobenzotriazole (ABTA) as a Removable Directing Group for Palladium-Catalyzed Aerobic Oxidative C-H Olefination.

Wang Zhuo Z Ye Xiaohan X Jin Meina M Tang Qi Q Fan Shengyu S Song Zhiguang Z Shi Xiaodong X

Organic letters 20220324 17

4-Aminobenzotriazole (ABTA) was applied as an effective removable directing group (DG) in Pd-catalyzed C-H activation for the first time. Compared with the widely applied pyridine and quinoline analogs, ABTA showed significantly improved reactivity, achieving aerobic oxidative C-H olefination in excellent yields (up to 95% vs <50% with other reported DGs under identical conditions). Using this new strategy, macrocyclization was achieved to give cyclic peptides in good yields with easy ABTA remov ...[more]

PMID: 35324203

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