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Lewis Acid-Assisted Transition Metal-Free Aminocyanation of Alkynes with Arylamines and N-Cyanosuccinimide
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2022-06-17 , DOI: 10.1002/adsc.202200376 Indranil Chatterjee 1 , Gautam Kumar 2 , Debkanta Bhattacharya 2
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2022-06-17 , DOI: 10.1002/adsc.202200376 Indranil Chatterjee 1 , Gautam Kumar 2 , Debkanta Bhattacharya 2
Affiliation
A transition-metal-free aminocyanation of aryl alkynes has been achieved using indium tribromide, InBr3 or B(C6F5)3 as a Lewis acid. This aminocyanation protocol features with non-toxic cyanide source, a good substrate scope and potentially valuable aminocyanation products. Mechanistic studies reveal the complex formation between Lewis acid and alkyne to produce in situ alkyne nitrile as a key intermediate. Further hydroamination of alkyne nitrile with arylamines affords the E-selective (E:Z=70:30 to 90:10) β-aminoacrylonitrile derivatives.
中文翻译:
路易斯酸辅助的芳胺和 N-氰基琥珀酰亚胺对炔烃的无金属氨基氰化反应
使用三溴化铟、InBr 3或 B(C 6 F 5 ) 3作为路易斯酸已经实现了芳基炔烃的无过渡金属氨基氰化。该氨基氰化方案具有无毒氰化物源、良好的底物范围和潜在有价值的氨基氰化产品的特点。机理研究揭示了路易斯酸和炔烃之间的复合物形成原位炔腈作为关键中间体。炔腈与芳胺的进一步加氢胺化得到E-选择性 ( E : Z =70:30 至 90:10) β-氨基丙烯腈衍生物。
更新日期:2022-06-17
中文翻译:
路易斯酸辅助的芳胺和 N-氰基琥珀酰亚胺对炔烃的无金属氨基氰化反应
使用三溴化铟、InBr 3或 B(C 6 F 5 ) 3作为路易斯酸已经实现了芳基炔烃的无过渡金属氨基氰化。该氨基氰化方案具有无毒氰化物源、良好的底物范围和潜在有价值的氨基氰化产品的特点。机理研究揭示了路易斯酸和炔烃之间的复合物形成原位炔腈作为关键中间体。炔腈与芳胺的进一步加氢胺化得到E-选择性 ( E : Z =70:30 至 90:10) β-氨基丙烯腈衍生物。