An efficient synthesis of amides and esters via triacyloxyboranes
An efficient synthesis of amides and esters via triacyloxyboranes
复制标题
DOI：
10.1055/s-2007-973890
复制
发表时间：
2007-04-24
期刊：
影响因子：
2
通讯作者：
Buckle, Ronald N.
中科院分区：
文献类型：
--
作者：
Huang, Zhongping;Reilly, John E.;Buckle, Ronald N.
硼烷-四氢呋喃络合物或硼烷-甲硫醚络合物用于活化羧酸以生成三酰氧基硼烷。三酰氧基硼烷可以有效地与各种亲核试剂包括烷基胺、芳基胺、酰肼、醇和酚在甲苯中回流反应，以优异的产率提供相应的酰胺和酯。脂肪族羧酸在芳族羧酸存在下在硼烷条件下选择性酯化。
Borane-tetrahydrofuran complex or borane-methyl sulfide complex is used to activate carboxylic acids to generate triacyloxyboranes. The triacyloxyboranes can be effectively reacted with various nucleophiles including alkylamines, arylamines, bydrazides, alcohols and phenols at reflux in toluene to provide the corresponding amides and esters in excellent yield. Aliphatic carboxylic acids are selectively esterified in the presence of aromatic carboxylic acids under the borane conditions.