Template Synthesis to Solve the Unreachable Ortho C-H Functionalization Reaction of Aryl Iodide

This report describes the use of a simple Pd/NBE catalytic system to achieve ortho C-H oxylation and phosphonylation and other functionalizations of aryl iodide through templated conversion reactions. Dimethylamine is introduced in the ortho-site of aryl iodide through C-H amination, and aryl dimethylamine is quickly converted to methyl quaternary ammonium salt precipitation. Methyl quaternary ammonium salt avoids Hofmann elimination in subsequent functionalization. This method solves various ortho functionalization reactions of aryl iodide that have not been achieved for a long time in the field of Pd/NBE chemistry indirectly.

Automated summary

This report describes a method that utilizes a simple Pd/NBE catalytic system to achieve ortho functionalization of aryl iodide. By introducing dimethylamine and converting it to methyl quaternary ammonium salt, this method solves a long-standing problem in this field.