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Letter

Iodine as a Chemoselective Reoxidant of TEMPO: Application to the Oxidation of Alcohols to Aldehydes and Ketones

Ross A. Miller* and R. Scott Hoerrner

Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065

Org. Lett., 2003, 5 (3), pp 285–287

DOI: 10.1021/ol0272444

Publication Date (Web): January 4, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ross_miller@merck.com

Abstract

Chemoselective alcohol oxidations using catalytic TEMPO and stoichiometric iodine as the terminal oxidant were studied. Iodine was compared to other positive halogens as the terminal oxidant and shown to be superior in cases of electron-rich and heteroaromatic rings. The new conditions were successfully applied to an important intermediate (2) in the synthesis of Losartan.

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Published In Issue February 06, 2003
Received November 6, 2002

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Letter

Iodine as a Chemoselective Reoxidant of TEMPO: Application to the Oxidation of Alcohols to Aldehydes and Ketones