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Synthesis 2013; 45(11): 1529-1533
DOI: 10.1055/s-0033-1338423
paper
© Georg Thieme Verlag Stuttgart · New York

Mn(OAc)3-Mediated Selective Free Radical Phosphonylation of Pyridinones and Pyrimidinones

Wang-Bin Sun
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 199 Renai Street, Suzhou, Jiangsu 215123, P. R. of China   Fax: +86(512)65880335   Email: jpzou@suda.edu.cn
,
Yun-Fei Ji
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 199 Renai Street, Suzhou, Jiangsu 215123, P. R. of China   Fax: +86(512)65880335   Email: jpzou@suda.edu.cn
,
Xiang-Qiang Pan
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 199 Renai Street, Suzhou, Jiangsu 215123, P. R. of China   Fax: +86(512)65880335   Email: jpzou@suda.edu.cn
,
Shao-Fang Zhou
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 199 Renai Street, Suzhou, Jiangsu 215123, P. R. of China   Fax: +86(512)65880335   Email: jpzou@suda.edu.cn
,
Jian-Ping Zou*
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 199 Renai Street, Suzhou, Jiangsu 215123, P. R. of China   Fax: +86(512)65880335   Email: jpzou@suda.edu.cn
b   Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Ling Ling Road 345, Shanghai 200032, P. R. of China
,
Wei Zhang*
c   Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA   Fax: +1(617)2876030   Email: wei2.zhang@umb.edu
,
Olayinkataiwo Asekun
d   Department of Chemistry, University of Lagos, Akoka, Yaba, Nigeria
› Author Affiliations
Further Information

Publication History

Received: 27 January 2013

Accepted after revision: 26 March 2013

Publication Date:
29 April 2013 (online)

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Abstract

The phosphonyl radical generated from the reaction of dimethyl phosphite with manganese(III) acetate adds selectively to the 3-position of pyridin-2-ones or the 5-position of pyrimidin-4-ones to afford phosphonylated products in good yields.

Key words

manganese(III) acetate - phosphonylation - pyridinone - pyrimidinone - dialkyl phosphite - free radical

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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