Peroxy mediated Csp2–Csp3 dehydrogenative coupling: regioselective functionalization of coumarins and coumarin-3-carboxylic acids†,Organic & Biomolecular Chemistry

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Peroxy mediated Csp2–Csp3 dehydrogenative coupling: regioselective functionalization of coumarins and coumarin-3-carboxylic acids†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-04-07 00:00:00 , DOI: 10.1039/c7ob02771k
Farnaz Jafarpour _{1,

2,

3,

4,

5} , Masoumeh Darvishmolla _{1,

2,

3,

4,

5}

Affiliation

A regioselective direct alkylation of coumarins at C-3 via cross-dehydrogenative coupling of unactivated Csp²–Csp³ bonds is developed. This protocol employs tert-butyl hydroperoxide as the sole reagent of the reaction to combine coumarins and ethers in reasonable yields under metal- and solvent-free reaction conditions. This protocol also worked well with coumarin-3-carboxylic acids to unveil a rare instance of a catalyst-free tandem alkylation/decarboxylation reaction with conservation of the double bond.

中文翻译：

过氧介导的Csp ² –Csp ³脱氢偶联：香豆素和香豆素-3-羧酸的区域选择性功能化†

通过未活化的Csp ² –Csp ³键的交叉脱氢偶联，开发了香豆素在C-3上的区域选择性直接烷基化反应。该方案使用叔丁基氢过氧化物作为反应的唯一试剂，以在无金属和无溶剂的反应条件下以合理的收率结合香豆素和醚。该方案还与香豆素-3-羧酸一起使用，揭示了一种罕见的无催化剂的串联双烷基化/脱羧反应，并保留了双键。

更新日期：2018-04-07

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