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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

Sneha Nandy, Avishek Ghatak, Asit Kumar Das, Sanjay Bhar*

*Department of Chemistry, Organic Chemistry Section, Jadavpur University, Kolkata-700032, India, Email: sanjay.bharjadavpuruniversity.in

S. Nandy, A. Ghatak, A. K. Das, S. Bhar, Synlett, 2018, 29, 2208-2212.

DOI: 10.1055/s-0037-1610247 (free Supporting Information)


Abstract

The use of tert-butyl hydroperoxide (TBHP) as a terminal oxidant in the presence of catalytic amount of tetrabutylammonium iodide and imidazole enables a transition-metal-free synthesis of aryl esters in high yield starting from benzylic primary alcohols and aliphatic alcohols. These reactions are highly chemoselective and tolerate a wide range of substituents.

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Key Words

aqueous reaction, chemoselectivity, TBHP, green chemistry, esters, oxidation


ID: J72-Y2018