Borane-Catalyzed Divergent para and ortho C-Alkylation of Arylamines Using Benzylic Alcohols

Abstract

A catalyst-controlled divergent alkylation of diarylamines with benzylic alcohols has been developed. A para C-alkylation of diarylamines could be achieved by using B(C₆F₅)₃ as the catalyst, whereas ortho C-alkylation of diarylamines could be achieved by using HBF₄·Et₂O as the catalyst. The salient features of this transformation include readily available materials, a broad substrate scope, easily available catalysts, and simple and mild reaction conditions.

Key words

Friedel–Crafts reaction - alkylation - arylamines - benzylic alcohols - divergent synthesis - borane catalysis

Publication History

Received: 28 July 2024

Accepted after revision: 27 August 2024

Accepted Manuscript online:
27 August 2024

Article published online:
26 September 2024

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