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Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides

Zheng Yang, Wen-Juan Hao*, Shu-Liang Wang, Jin-Peng Zhang, Bo Jiang*, Guigen Li and Shu-Jiang Tu*

*School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, People’s Republic of China, Email: wjhaojsnu.edu.cn, jiangchemjsnu.edu.cn, laotujsnu.edu.cn

Z. Yang, W.-J. Hao, S.-L. Wang, J.-P. Zhang, B. Jiang, G. Li, S.-J. Tu, J. Org. Chem., 2015, 80, 9224-9230.

DOI: 10.1021/acs.joc.5b01684 (free Supporting Information)


 
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Abstract

A TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc provides allenyl sulfones in good yields in a short reaction time via HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. This reaction shows highly functional group compatibility and excellent regioselectivity.

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Key Words

sulfones, allenes, TBHP


ID: J42-Y2015