钯(II)催化的非手性亚甲基 C(sp3)-H 键的对映选择性芳基化反应，由 3,3'-F-BINOL 配体实现。
Pd(II)-Catalyzed enantioselective arylation of unbiased methylene C(sp)-H bonds enabled by a 3,3'-F-BINOL ligand.
机构信息
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020, China.
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China.
出版信息
Chem Commun (Camb). 2021 Jun 3;57(45):5562-5565. doi: 10.1039/d1cc01690c.
Palladium-catalyzed asymmetric functionalization of unbiased methylene C(sp3)-H bonds is a long-standing challenge. Here, we report a Pd(ii)-catalyzed highly enantioselective arylation of unbiased methylene C(sp3)-H bonds enabled by a strongly coordinating bidentate 2-pyridinylisopropyl (PIP) directing group and an easily accessible 3,3'-F2-BINOL chiral ligand. The use of aryl iodides with the combination of 3,3'-F2-BINOL was beneficial for high enantiocontrol. A range of aliphatic amides and aryl iodides were tolerated, providing the desired arylated products in high enantioselectivities (up to 96% ee). The PIP directing group could be removed under mild conditions without erosion of enantiopurity.
钯催化的非导向亚甲基 C(sp3)-H 键不对称功能化是一个长期存在的挑战。在这里，我们报道了一种钯(ii)催化的高度对映选择性芳基化反应，该反应通过强配位的双齿 2-吡啶基异丙基 (PIP)导向基团和易于获得的 3,3'-F2-BINOL 手性配体实现。使用芳基碘化物与 3,3'-F2-BINOL 的组合有利于高对映控制。一系列脂肪族酰胺和芳基碘化物都可以耐受，以高对映选择性（高达 96%ee）提供所需的芳基化产物。在温和条件下可以去除 PIP 导向基团，而不会破坏对映体纯度。
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