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Palladium‐Catalyzed Decarboxylative Cross‐Couplings of 1‐Boc‐3‐iodoazetidine: Regioselective Access to 2‐Alkynylazetidines, 3‐Alkynylazetidines and 3‐Vinylazetidines
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-05-02 , DOI: 10.1002/adsc.201800100
Shuaijun Han 1 , Xiaoxiao Ren 1 , Qingsong Wu 1 , Apeng Liang 1 , Jingya Li 2 , Dapeng Zou 1 , Yangjie Wu 1 , Yusheng Wu 1, 2, 3
Affiliation  

The first palladium‐catalyzed decarboxylative coupling reactions of alkynyl carboxylic acids or α, β‐unsaturated carboxylic acids with 1‐Boc‐3‐iodoazetidine were described. The strategy could efficiently mediate β‐hydride elimination/migratory insertion sequence and selectively form 2‐alkynylazetidines (10 examples) and 3‐alkynylazetidines (15 examples) with high regioselectivity. The protocol provides convienient access to a variety of useful 3‐vinylazetidines in moderate yields (42%–72%) with good stereoselectivity. Notable advantages of this method include easy operation, mild reaction conditions, and wide substrate scope.

中文翻译:

1-Boc-3-碘氮杂环丁烷的钯催化脱羧交叉偶联:对2-炔基氮杂环丁烷,3-炔基氮杂环丁烷和3-乙烯基氮杂环丁烷的区域选择性访问

描述了炔基羧酸或α,β-不饱和羧酸与1-Boc-3-碘氮杂环丁烷的钯催化的第一个脱羧偶联反应。该策略可以有效地介导β-氢化物消除/迁移插入序列,并选择性地形成具有高区域选择性的2-炔基氮杂环丁烷(10个实例)和3-炔基氮杂环丁烷(15个实例)。该协议以适中的收率(42%–72%)和良好的立体选择性,使人们可以方便地获得各种有用的3-乙烯基氮杂环丁烷。该方法的显着优点包括操作简便,反应条件温和以及底物范围广。
更新日期:2018-05-02
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