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Chemoselective and Metal-Free Synthesis of Aryl Esters from the Corresponding Benzylic Alcohols in Aqueous Medium Using TBHP/TBAI as an Efficient Catalytic System
Synlett ( IF 1.7 ) Pub Date : 2018-09-12 , DOI: 10.1055/s-0037-1610247
Sanjay Bhar 1 , Sneha Nandy 1 , Avishek Ghatak 2 , Asit Das 3
Affiliation  

A novel and transition-metal-free strategy has been developed for the synthesis of aryl esters starting from corresponding benzylic primary alcohols as the exclusive substrates using tert-butyl hydroperoxide (TBHP) as a terminal oxidant in the presence of catalytic amount of tetrabutylammonium iodide (TBAI) and imidazole, where the aliphatic alcohols remained unaffected. These reactions are highly chemoselective and associated with high yield and wide applicability accommodating a wide range of substituents. Excellent chemoselectivity has also been demonstrated through intramolecular competition experiments. This protocol can be considered as an important analogue of Tishchenko reaction using benzylic alcohols as the substrates instead of benzaldehydes.

中文翻译:

使用 TBHP/TBAI 作为高效催化体系,从相应的苯甲醇在水性介质中化学选择性和无金属合成芳基酯

在催化量的四丁基碘化铵存在下,使用叔丁基过氧化氢(TBHP)作为末端氧化剂,以相应的苄基伯醇为唯一底物,开发了一种新的无过渡金属的合成芳基酯的策略。 TBAI) 和咪唑,其中脂肪醇不受影响。这些反应具有高度的化学选择性,并且具有高产率和广泛的适用性,可容纳多种取代基。通过分子内竞争实验也证明了优异的化学选择性。该协议可以被视为使用苯甲醇作为底物而不是苯甲醛的 Tishchenko 反应的重要类似物。
更新日期:2018-09-12
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