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Fe(III)-Based Tandem Catalysis for Amidomethylative Multiple Substitution Reactions of α-Substituted Styrene Derivatives
ACS Catalysis ( IF 12.9 ) Pub Date : 2020-08-25 , DOI: 10.1021/acscatal.0c02676
Xiaolin Qian 1 , Hui Zhou 1 , Hetti Handi Chaminda Lakmal 1 , James Lucore 1 , Xuesong Wang 1 , Henry U. Valle 1 , Bruno Donnadieu 1 , Xue Xu 1 , Xin Cui 1
Affiliation  

Developing tandem multiple C–H substitution reactions of simple alkenes provides rapid access to structurally complex unsaturated building blocks. Amidomethylative reactions that reserve C═C double bonds have been composed sequentially for tandem catalytic substitutions around the C═C bonds of alkenes. As a proof-of-concept demonstration, tandem catalytic amidomethylative processes, which effectively form multiple C–C bonds, have been developed to directly and selectively transform α-substituted styrenes into unsaturated N-heterocycles. Using Fe(OTf)3 as the sole catalyst, the operationally simple protocols employ bench-stable bisamidomethane as the sole reagent to produce hexahydropyrimidines and 1,2,3,6-tetrahydropyridine derivatives. Moreover, the practical catalytic processes constituted facile two-step pathways, from simple α-substituted styrenes, to access unsaturated 1,3-diamine and bispidine derivatives.

中文翻译:

基于Fe(III)的串联催化,用于α取代的苯乙烯衍生物的酰胺甲基化多次取代反应

开发简单烯烃的串联多个C–H取代反应可快速进入结构复杂的不饱和结构单元。保留C═C双键的酰胺甲基化反应已顺序进行,以围绕烯烃的C═C键进行串联催化取代。作为概念验证,已经开发出可有效形成多个C–C键的串联催化氨基甲基化方法,可直接和选择性地将α-取代的苯乙烯转化为不饱和N-杂环。使用Fe(OTf)3作为唯一的催化剂,操作简单的方案采用稳定的双酰胺基甲烷作为唯一的试剂来生产六氢嘧啶和1,2,3,6-四氢吡啶衍生物。而且,实际的催化过程构成了从简单的α-取代的苯乙烯到不饱和的1,3-二胺和联吡啶的两步路线。
更新日期:2020-09-20
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