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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.

DOI:10.1021/acs.joc.1c01629
PMID:34699223
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8576819/
Abstract

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%.

摘要

已开发出一种通过苯并磷杂环戊-3-基三氟甲磺酸酯开环合成2-乙炔基苯基（二芳基）氧化膦的新的简便方法。该过程通过格氏试剂在磷中心的亲核进攻发生，这导致环的打开和离去基团的裂解。反应在温和条件下进行，在15 - 60分钟内，可得到一系列以前无法获得的2-乙炔基苯基氧化膦，产率高达98%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/6ff3f68ecf99/jo1c01629_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/c924648dd1de/jo1c01629_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/8c406398e891/jo1c01629_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/28488a330994/jo1c01629_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/c14691611943/jo1c01629_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/878988b6e30d/jo1c01629_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/fc2c83693411/jo1c01629_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/6ff3f68ecf99/jo1c01629_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/c924648dd1de/jo1c01629_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/8c406398e891/jo1c01629_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/28488a330994/jo1c01629_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/c14691611943/jo1c01629_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/878988b6e30d/jo1c01629_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/fc2c83693411/jo1c01629_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/acfb/8576819/6ff3f68ecf99/jo1c01629_0007.jpg

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