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Transition‐Metal‐Free Base‐Controlled C−N Coupling Reactions: Selective Mono Versus Diarylation of Primary Amines with 2‐Chlorobenzimidazoles
Author(s) -
Sang Wei,
Gong YanYan,
Cheng Hua,
Zhang Rui,
Yuan Ye,
Fan GuangGao,
Wang ZhiQin,
Chen Cheng,
Verpoort Francis
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001365
Subject(s) - chemistry , primary (astronomy) , base (topology) , transition metal , selectivity , coupling (piping) , combinatorial chemistry , metal , base metal , medicinal chemistry , stereochemistry , organic chemistry , catalysis , metallurgy , mathematical analysis , physics , materials science , mathematics , astronomy , welding
Herein, a base‐controlled protocol was developed for the C−N coupling of primary amines and 2‐chlorobenzimidazoles, affording a handful of secondary or tertiary amines in a selective fashion. Moreover, this protocol was realized under transition‐metal‐free conditions, and the variation of the base from i Pr 2 NH to LiO t Bu completely switched the selectivity from monoarylation to diarylation. Further investigations elucidated that the variety, intrinsic basicity and amount of the utilized bases considerably affected these reactions.