Synlett 2025; 36(06): 739-743
DOI: 10.1055/a-2404-2285
letter

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

Hao-Lan Hu
a   Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China
,
Peng Chen
a   Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China
,
Yu-Dan Niu
a   Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China
,
Meng-Yuan Li
a   Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China
,
Jianghuan Shi
b   Ningbo Institute of Measurement and Testing (Ningbo Inspection and Testing Center for New Materials), Ningbo 315048, P. R. of China
,
Yi-Jun Jiang
a   Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China
› Author Affiliations
This research was supported by Zhejiang Provincial Natural Science Foundation of China (Grant No. LY23B040001) and Programs Supported by Ningbo Natural Science Foundation (Grant No. 202003N4009).


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.

Supporting Information



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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