Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 14
580
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

Catalytic Oxidation of Alcohols to Corresponding Aldehydes or Ketones with TEMPO-Mediated Iodosobenzene in Water in the Presence of a Surfactant

, &
Pages 2057-2066 | Received 13 Apr 2009, Published online: 17 Jun 2010
 

Abstract

An efficient, facile, and rapid oxidation of alcohols to the corresponding aldehydes or ketones with a stoichiometric amount of iodosobenzene (PhIO) in the presence of catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl free radical (TEMPO), KBr, and a surfactant, such as SDS (sodium dodecylsulfate), was reported. The oxidation proceeded in water at room temperature to afford aldehydes or ketones in excellent yields and high selectivity without overoxidation to carboxylic acids. Selective oxidation of primary alcohols in the presence of secondary alcohols was also achieved with the catalytic system of PhIO/TEMPO/KBr/SDS. A possible mechanism for the oxidation was supposed.

ACKNOWLEDGMENT

We are grateful to Nanjing University of Science and Technology for financial support.

Notes

a Reaction conditions: p-nitrobenzyl alcohol (1 mmol), PhIO (2.2 mmol), TEMPO (0.1 mmol), KBr (0.2 mmol), surfactant (0.2 mmol), water (5 mL) at room temperature for 2 h.

b Calculated according to Davis law.

c GC conversion and selectivity.

d Isolated yield.

e 0.1 g Tween-80 was added.

a Reaction conditions: alcohol (1 mmol), PhIO (2.2 mmol), TEMPO (0.1 mmol), KBr (0.2 mmol), surfactant (0.2 mmol), and water(5 mL) at room temperature.

b GC conversion.

c Yields of isolated products unless otherwise noted.

d Yields were determined by GC.

a The reactions were carried out on a 1:1 mixture of primary and secondary alcohols, on a 1-mmol scale.

b Isolated yield.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.