Iodine as a chemoselective reoxidant of TEMPO: application to the oxidation of alcohols to aldehydes and ketones.
[reaction: see text] 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.
Miller
Ross A
RA
Merck Research Laboratories, PO Box 2000, Rahway, New Jersey 07065, USA. ross_miller@merck.com
Hoerrner
R Scott
RS
D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D019808:Losartan / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction
D000438:Alcohols; D000447:Aldehydes; D003497:Cyclic N-Oxides; D007659:Ketones; D016877:Oxidants; D007455:Iodine; D019808:Losartan; C003959:TEMPO