Ding Chao, Ren Yaoyu, Yu Yue, Yin Guoyin
The Institute for Advanced Studies, Wuhan University, 430072, Wuhan, Hubei, People's Republic of China.
Nat Commun. 2023 Nov 23;14(1):7670. doi: 10.1038/s41467-023-43642-z.
Organosilicon compounds have shown tremendous potential in drug discovery and their synthesis stimulates wide interest. Multicomponent cross-coupling of alkenes with silicon reagents is used to yield complex silicon-containing compounds from readily accessible feedstock chemicals but the reaction with simple alkenes remains challenging. Here, we report a regioselective silylalkylation of simple alkenes, which is enabled by using a stable Ni(II) salt and an inexpensive trans-1,2-diaminocyclohexane ligand as a catalyst. Remarkably, this reaction can tolerate a broad range of olefins bearing various functional groups, including alcohol, ester, amides and ethers, thus it allows for the efficient and selective assembly of a diverse range of bifunctional organosilicon building blocks from terminal alkenes, alkyl halides and the Suginome reagent. Moreover, an expedient synthetic route toward alpha-Lipoic acid has been developed by this methodology.
有机硅化合物在药物发现中已显示出巨大潜力，其合成引发了广泛关注。烯烃与硅试剂的多组分交叉偶联用于从易于获得的原料化学品中制备复杂的含硅化合物，但与简单烯烃的反应仍然具有挑战性。在此，我们报道了一种简单烯烃的区域选择性硅烷基化反应，该反应通过使用稳定的镍（II）盐和廉价的反式-1,2-二氨基环己烷配体作为催化剂来实现。值得注意的是，该反应能够耐受带有各种官能团的多种烯烃，包括醇、酯、酰胺和醚，因此它允许从末端烯烃、卤代烃和杉野试剂高效且选择性地组装各种双官能有机硅结构单元。此外，通过这种方法开发了一条通往α-硫辛酸的便捷合成路线。
