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A Simple, Mild and Efficient Oxidation of Benzylic Alcohols in the Presence of NBS/KOAc in Aqueous Solution

Abstract: Background: The oxidation of benzylic alcohols to carbonyl compounds is a fundamental reaction in organic synthesis. In traditional oxidation processes, a large amount of toxic and volatile organic solvents and metal oxidants are used. Thus, developing environmentally benign oxidation processes is an important goal. N-Bromosuccinimide (NBS) is an inexpensive and convenient oxidant widely used in a variety of oxidative reactions under acidic or alkaline conditions.

Methods: In this paper, we developed a simple, mild, and efficient oxidation of benzylic alcohols in the presence of N-bromosuccinimide (NBS)/KOAc in aqueous solution (H2O/CH2Cl2 = 3:1).

Results: A series of benzylic alcohols were oxidized selectively to the corresponding ketones in moderate to excellent yields at room temperature.

Conclusion: This reaction was carried out using a wide variety of substrates, required no metal catalyst, and proved to be tolerant towards a variety of different functional groups.

Authors:   Wu, Jianglong; Liu, Yan; Liu, Ping; Gu, Chengzhi
Journal:   Letters in Organic Chemistry
DOI:   10.2174/1570178614666170221142818
Facts, background information, dossiers
  • temperature
  • substrates
  • paper
  • functional groups
  • carbonyl compounds
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