Proton Transfer Can Govern Regioselectivity Assisted by Iron Catalysis.

ABSTRACT: Ortho-selective aromatic C-H functionalization is frequently used in organic synthesis and chemical/pharmaceutical industries. However, this reaction relies heavily on the use of directing groups suffering from limited substrate scope and extra steps to put on and remove the directing/protecting groups. Herein we present the previously neglected concept that enables good to nearly complete selective ortho position. Proton transfer was utilized to tune the electron density on the aryl ring and determine the positional selectivity of electrophilic substitution. Consistently with deuteration experiments and DFT studies, this work demonstrates that acid-promoted proton transfer directs accelerated ortho-selective halogenation of NH/OH contained aromatic amines/phenols with excellent selectivit

SUBMITTER: Li Y 

PROVIDER: S-EPMC7298526 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature