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Two‐in‐One Strategy for Palladium‐Catalyzed C−H Functionalization in Water
Author(s) -
Zeng Huiying,
Wang Zemin,
Li ChaoJun
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813391
Subject(s) - surface modification , chemistry , catalysis , palladium , reagent , pyridine , combinatorial chemistry , tryptamine , transition metal , organic chemistry , biochemistry
Transition metal catalyzed C−H functionalizations have been developed as powerful methods for C−C bond formations. Directing groups, removable directing groups, traceless directing groups, and transient directing groups (TDGs) have been successfully used to improve the reaction efficiencies. For the development of greener and more sustainable methods, C−H functionalization using a TDG that also serves as a reagent in aqueous solvent was investigated. The palladium‐catalyzed C−H functionalization of tryptamine derivatives using ketones in water successfully generated tetrahydro‐β‐carbolines with a quaternary carbon center at C1. Deuterium‐labeling experiments are discussed to provide insight into the mechanism. The C2‐position of pyridine was also successfully functionalized by this strategy.