通过芳基格氏试剂使苯并磷杂环戊烷-3-酮氧化物衍生的三氟甲磺酸酯开环作为制备2-乙炔基苯基(二芳基)氧化膦的一条途径。

Ring Opening of Triflates Derived from Benzophospholan-3-one Oxides by Aryl Grignard Reagents as a Route to 2-Ethynylphenyl(diaryl)phosphine Oxides.

作者信息

Ponikiewski Łukasz, Sowa Sylwia

机构信息

Department of Inorganic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, G. Narutowicza St. 11/12, Gdańsk PL-80-233, Poland.

Department of Organic Chemistry, Faculty of Chemistry, Institute of Chemical Sciences, Marie Curie-Sklodowska University in Lublin, 33 Gliniana Street, Lublin PL-20-614, Poland.

出版信息

J Org Chem. 2021 Nov 5;86(21):14928-14941. doi: 10.1021/acs.joc.1c01629. Epub 2021 Oct 26.

A new simple method for the synthesis of 2-ethynylphenyl(diaryl)phosphine oxides via ring opening of benzophosphol-3-yl triflates has been developed. This process occurs via nucleophilic attack of a Grignard reagent at the phosphorus center, which results in ring opening and cleavage of a leaving group. The reaction proceeds under mild conditions and, within 15-60 min, leads to a library of previously unavailable 2-ethynylphenylphosphine oxides in yields up to 98%.