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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

Authors

  • 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

This project was supported by the Fundamental Research Funds for the Central Universities (NJAU, Grant No. KYTZ201604).
Further Information

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