Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 16, Pages 7357-7365Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c00936
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Funding
- Monash University [S02802-3950366]
- Natural Science Foundation of Jiangsu Province, China [BK20210105]
- Ministry of Education, Science, and Technological Development of the Republic of Serbia [451-03-68/2022-14/200146]
- Nanjing Tech University [39837123, 39837132]
- Natural Science Foundation of Jiangsu Province [BK20211587]
- National Natural Science Foundation of China [21973044]
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Introducing a small phosphorus-based fragment into molecules via trapping and releasing reactive phosphorus-based molecules is an important process in synthetic chemistry. This study used electron-rich hexaphenylcarbodiphosphorane to stabilize the least thermodynamically favorable isomer of HO2P and transfer it to various substrates. Additionally, several phosphorus-based compounds were isolated and characterized using this synthetic approach.
Introducing a small phosphorus-based fragment into other molecular entities via, for example, phosphorylation/phosphonylation is an important process in synthetic chemistry. One of the approaches to achieve this is by trapping and subsequently releasing extremely reactive phosphorus-based molecules such as dioxophosphoranes. In this work, electron-rich hexaphenylcarbodiphosphorane (CDP) was used to stabilize the least thermodynamically favorable isomer of HO2P to yield monomeric CDP center dot PHO2. The title compound was observed to be a quite versatile phosphonylating agent; that is, it showed a great ability to transfer, for the first time, the HPO2 fragment to a number of substrates such as alcohols, amines, carboxylic acids, and water. Several phosphorous-based compounds that were generated using this synthetic approach were also isolated and characterized for the first time. According to the initial computational studies, the addition-elimination pathway was significantly more favorable than the corresponding elimination-addition route for delivering the HO2P unit in these reactions.
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