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Enaminones is an important class of functional olefins, due to its both the nucleophilicity of enamine and the electrophilicity of enone, it is often used in the synthesis of nitrogen-containing monoheterocyclic compounds, and as a potential pharmaceutical synthesis intermediate, enamine is also an important component of
many pharmacologically active compounds.
Cross-dehydrogenative-coupling (CDC) reaction is an ideal strategy for directly constructing carbon-carbon bonds or carbon-heterobonds, which does not require pre-functionalization and by-products are only hydrogen or water, with simple synthesis, Green environmental protection and other advantages
.
In recent years, the direct construction of polyfunctional enamine compounds through CDC strategies has attracted a lot of attention, and at present, the existing research has mainly focused on the functionalization of enamine C(sp2)-H bonds, while the more challenging C(sp3)-H is more challenging Key functionalization reactions have not been reported
.
Recently, the Li Shenghong special group of Kunming Institute of Botany, Chinese Academy of Sciences developed a non-metallic catalytic region-selective cross-coupling dehydrogenation reaction between enamine and heterocyclic thiol, which realized the direct functional grouping
of enamine γ-C(sp 3)-H bonds for the first time.
The strategy uses cheap and readily available KIO3 as the catalyst and air as the only oxidant, which has the advantages
of mild conditions, green environmental protection, high atomic economy, high regional selectivity, and good functional group tolerance.
In addition, the method enables efficient preparation at gram scale while also showing good applicability in the late modification of complex natural products and drug molecules
.
This work provides a new strategy for the green and efficient construction of carbon-sulfur bonds and the structural modification of complex active molecules (Figure 1).
Figure 1 γ-C(sp3)-H functional grouping reaction of enamine
The results of the related research are KIO 3-Mediatedγ-C(sp3)-H Sulfenylation of Enaminones Published in Organic Letters, an authoritative journal in organic chemistry (2022, 24, 7533-7537; Doi: 10.
1021/acs.
orglett.
2c02824）
。 Zheng Yu, a postdoctoral fellow at the station, is the first author of the paper, researcher Li Shenghong is the corresponding author, and the Kunming Institute of Botany, Chinese Academy of Sciences is the first
.
The research was supported by the National Natural Science Foundation of China Key Program (21937006), the National Natural Science Foundation of China Youth Fund Project (22101287), the Yunnan Postdoctoral Directed Training Funding Project, and the Yunnan Postdoctoral Research Fund Project.
Link to the article
