A Heteroarylamine Library: Indium-Catalyzed Nucleophilic Aromatic Substitution of Alkoxyheteroarenes with Amines
作者:Kyohei Yonekura、Yasuhiro Yoshimura、Mizuri Akehi、Teruhisa Tsuchimoto
DOI:10.1002/adsc.201701452
日期:2018.3.20
five‐membered heteroaryl electrophiles fused with/without a benzene ring were found to couple with amines to produce heteroarylamines with broad structural diversity. The heteroarylamine formation proceeds through the cleavage of a heteroaryl−OMe bond by the nucleophilic attack of the amine based on the nucleophilic aromatic substitution (SNAr) reaction. In contrast to the corresponding traditional SNAr amination
在铟路易斯酸催化下,与/不与苯环稠合的富电子五元杂芳基亲电试剂与胺偶合生成具有广泛结构多样性的杂芳基胺。通过基于亲核芳香取代(S胺的亲核攻击,通过杂芳基- OME键的裂解的杂芳基形成前进Ñ AR)反应。与相应的传统S N Ar胺形成对比,目前基于S N Ar的杂芳基胺化反应无需依赖具有吸电子基团的杂芳基亲电子试剂和亲核性增强的金属酰胺。对NO 2,Br,I,CF 3等官能团的高度相容性观察到CN,CO 2 Et,吡啶基,噻唑基,C = C和OH基团,从而表明该方法的实用性和可靠性。机理研究表明,在此过程中,杂芳基环上可能会形成碳-铟键。