Palladium-Catalyzed C(sp³ )-H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group.

ABSTRACT: C-H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C-H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C-H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detail

SUBMITTER: St John-Campbell S 

PROVIDER: S-EPMC6391947 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature