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

Yutaka Minamitsuji; Daishi Kato; Hiromichi Fujioka; Toshifumi Dohi; Yasuyuki Kita

doi:10.1071/CH09148

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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 and Yasuyuki Kita ^B ^C

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 62(7) 648-652 https://doi.org/10.1071/CH09148
Submitted: 13 March 2009 Accepted: 30 April 2009 Published: 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.

Acknowledgements

The present work was partially supported by a Grant-in-Aid for Scientific Research (A) and for Young Scientists (B), and a grant for Scientific Research on Priority Areas ‘Advanced Molecular Transformations of Carbon Resources’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. TD also acknowledges support from the Industrial Technology Research Grant Program from the New Energy and Industrial Technology Development Organization (NEDO) of Japan and the Japan Chemical Innovation Institute (JICC).

References

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

Abstract

Acknowledgements

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