Journal
ORGANIC LETTERS
Volume 24, Issue 6, Pages 1357-1361Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00048
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Funding
- National Key Research and Development Program of China [2021YFD1700102]
- National Natural Science Foundation of China [21907052]
- Fundamental Research Funds for the Central Universities [JCQY202107]
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In this study, a facile and efficient approach to achieve monofluoromethylsulfinyl alkylation of quinoxalinones was developed, which involved the construction of new C-C and C-S bonds through the cleavage of C-F bond. The proposed mechanism was confirmed by density functional theory calculations, and the reaction exhibited a high level of atom economy. Moreover, the obtained products showed excellent biological activity.
We developed a facile, efficient, and scalable route to achieve monofluoromethylsulfinyl alkylation of quinoxalinones. NaSO2CH2F served as the source of methylene to construct new C-C and C-S bonds via C-F bond cleavage. NaSO2CH2F was also the source of SO2CH2F. Density functional theory calculations confirmed the proposed mechanism, in which the SO2CH2F radical is immediately trapped. The reaction exhibited a high level of atom economy. Moreover, some representative products displayed excellent biological activity.
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