Cu (II) 2-quinoxalinol salen catalyzed oxidation of propargylic, benzylic, and allylic alcohols using tert-butyl hydroperoxide in aqueous solutions

Kushan C Weerasiri, Anne Gorden

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of carbonyl compounds by oxidation of alcohols is a key reaction in organic synthesis. Such oxidations are typically conducted using catalysts featuring toxic metals and hazardous organic solvents. Considering green and sustainable chemistry, a copper(II) complex of sulfonated 2-quinoxalinol salen (sulfosalqu) has been characterized as an efficient catalyst for the selective oxidation of propargylic, benzylic, and allylic alcohols to the corresponding carbonyl compounds in water when in combination with the oxidant tert-butyl hydroperoxide. The reactions proceed under mild conditions (70 °C in water) to produce yields up to 99% with only 1 mol % of catalyst loading. This reaction constitutes of a rare example of propargylic alcohol oxidation in water, and it makes this process greener by eliminating the use of hazardous organic solvents. Excellent selectivity was achieved with this catalytic protocol for the oxidation of propargylic, benzylic, and allylic alcohols
Original languageEnglish
Pages (from-to)7962--7968
JournalTetrahedron
DOIs
StatePublished - 2014

Fingerprint Dive into the research topics of 'Cu (II) 2-quinoxalinol salen catalyzed oxidation of propargylic, benzylic, and allylic alcohols using tert-butyl hydroperoxide in aqueous solutions'. Together they form a unique fingerprint.

Cite this