Organoiodine-Catalyzed Oxidative Spirocyclization of Phenols using Peracetic Acid as a Green and Economic Terminal Oxidant

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Contents Vol 62(7)

doi:10.1071/CH09148

Organoiodine-Catalyzed Oxidative Spirocyclization of Phenols using Peracetic Acid as a Green and Economic Terminal Oxidant

Yutaka Minamitsuji ^A, Daishi Kato ^B, Hiromichi Fujioka ^A, Toshifumi Dohi ^A ^B, Yasuyuki Kita ^B ^C

^A Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan.
^B College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan.
^C Corresponding author. Email: kita@ph.ritsumei.ac.jp





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Australian Journal of Chemistry 62(7) 648–652 http://dx.doi.org/10.1071/CH09148
Submitted: 13 March 2009 Accepted: 30 April 2009 Published online: 13 July 2009

Abstract

The use of peracetic acid as a green and economical terminal oxidant in fluoroalcohol solvents could provide a practical iodoarene-catalyzed oxidation of phenols to give spirodienones. Acetic acid and water were the only co-products and waste, and thus this catalytic approach utilizing fluoroalcohol media could simplify the reaction workup procedure for product isolation.