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Silver-Catalyzed Intermolecular [3 + 2]/[5 + 2] Annulation of N-Arylpropiolamides with Vinyl Acids: Facile Synthesis of Fused 2H-Benzo[b]azepin-2-ones
ACS Catalysis ( IF 12.9 ) Pub Date : 2017-09-07 00:00:00 , DOI: 10.1021/acscatal.7b02061
Yang Li 1, 2 , Ming Hu 1, 2 , Jin-Heng Li 1, 2, 3
Affiliation  

A silver-catalyzed oxidative intermolecular [3 + 2]/[5 + 2] annulation of N-arylpropiolamides with 4-vinyl acids for producing fused 2H-benzo[b]azepin-2-ones is described. This radical-mediated annulation reaction features broad substrate scope and excellent selectivity, and enables the formation of three new C–C bonds through oxidative decarboxylation, [3 + 2]/[5 + 2] annulations, and C(sp2)-H functionalization cascades. Employing this silver-catalyzed oxidative strategy, common terminal alkynes were successfully converted into cyclopentenes via intermolecular [3 + 2] annulation.

中文翻译:

银催化的N-丙酰胺与乙烯基酸的分子间[3 + 2] / [5 + 2]环化:熔融合成2 H-苯并[ b ] azepin -2-ones的简便合成

描述了一种银催化的N-丙酰胺与4-乙烯基的氧化性分子间[3 + 2] / [5 + 2]环化反应,用于生产稠合的2 H-苯并[ b ]氮杂-2-酮。这种自由基介导的环化反应具有广泛的底物范围和出色的选择性,并能够通过氧化脱羧,[3 + 2] / [5 + 2]环化和C(sp 2)-H形成三个新的C–C键功能化级联。利用这种银催化的氧化策略,常见的末端炔烃通过分子间[3 + 2]环合成功地转化为环戊烯。
更新日期:2017-09-07
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