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Synthesis 2018; 50(15): 2990-2998
DOI: 10.1055/s-0037-1609835
special topic
© Georg Thieme Verlag Stuttgart · New York

Latent Radical Cleavage of α-Allenylic C–O Bonds: Potassium Persulfate Mediated Thiolation of Allenylphosphine Oxides

Kai Luo 
a   Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. of China   Email: rickywu@njau.edu.cn
b   Lab of Plant Stress Biology, College of Life Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. of China
,
Ling Zhang
a   Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. of China   Email: rickywu@njau.edu.cn
,
Kai Wei
a   Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. of China   Email: rickywu@njau.edu.cn
,
Wen-Chao Yang 
a   Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. of China   Email: rickywu@njau.edu.cn
,
Lei Wu  *
a   Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, P. R. of China   Email: rickywu@njau.edu.cn
c   Beijing National Laboratory for Molecular Sciences and Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
› Author AffiliationsThis project was supported by the Fundamental Research Funds for the Central Universities (NJAU, Grant No. KYTZ201604).
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Publication History

Received: 10 February 2018

Accepted after revision: 14 March 2018

Publication Date:
19 April 2018 (online)

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

A novel potassium persulfate (K2S2O8) mediated thiolation of allenylphosphine oxides with diaryl sulfides is disclosed. Mechanistic studies indicate that K2S2O8 homolyzes the diaryl sulfide to produce a thiyl radical (PhS•), which is followed by C–O bond cleavage of the allenylphosphine oxide under metal-free conditions, affording novel S,P-bifunctionalized butadienes in moderate to excellent yields.

Key words

potassium persulfate - thiolation - C–O bond cleavage - thiyl radical - S,P-bifunctionalized butadienes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609835.
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