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Transition‐Metal‐Free Selective C−H Benzylation of Tertiary Arylamines by a Dearomatization‐Aromatization Sequence
Author(s) -
Xu GuoQiang,
Feng ZhiTao,
Xu JiTao,
Wang ZhuYin,
Qin Yong,
Xu PengFei
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803211
Subject(s) - aromatization , transition metal , chemistry , benzene , molecule , substrate (aquarium) , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
Due to the significance of hybrid systems in drug discovery, there is an urgent need to assemble multiple biologically active ingredients into a single molecule. Here, we report a general transition‐metal‐free selective C−H benzylation of tertiary arylamines in good to excellent yields with a broad substrate scope and high functional‐group tolerance under mild conditions. Besides arylamines, some other benzene derivatives also readily furnished the corresponding diaryl methane derivatives with this protocol. A series of control experiments and theoretical calculations indicated that this transition‐metal‐free reaction is a dearomatization‐aromatization process.