Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Acetic Acid Mediated Sulfonylation of Allenylphosphine Oxides: Divergent Synthesis of Bifunctionalized 1,3-Butadienes and Allenes

Acetic Acid Mediated Sulfonylation of Allenylphosphine Oxides: Divergent Synthesis of Bifunctionalized 1,3-Butadienes and Allenes
Kai Luo, Qiang Sha, Lei Wu, Ling Zhang, Jing Ma
An acetic acid-mediated sulfonylation of allenylphosphine oxides with sodium sulfinates is disclosed. This new methodology involves tandem (Ar)O–C(sp3) bond cleavage and C(sp2)/C(sp3)–SO2 formation toward divergent synthesis of sulfonyl- and phosphinyl-bifunctionalized 1,3-butadienes or allenes, depending on the substitution at the terminal carbon atoms of allenylphosphine oxides. The reaction mechanism is explained via an acid-accelerated synergistic process.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00813

DOI: 10.1021/acs.joc.7b00813

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