对映选择合成
化学
恶唑啉
配体(生物化学)
催化作用
碘苯
金属化
二茂铁
立体化学
组合化学
芳基
药物化学
烷基
有机化学
受体
生物化学
电极
物理化学
电化学
作者
Xin Kuang,Jianjun Li,Tao Liu,Chang‐Hua Ding,Kevin Wu,Peng Wang,Jin‐Quan Yu
标识
DOI:10.1038/s41467-023-43278-z
摘要
Abstract A wide range of Cu(II)-catalyzed C–H activation reactions have been realized since 2006, however, whether a C–H metalation mechanism similar to Pd(II)-catalyzed C–H activation reaction is operating remains an open question. To address this question and ultimately develop ligand accelerated Cu(II)-catalyzed C–H activation reactions, realizing the enantioselective version and investigating the mechanism is critically important. With a modified chiral BINOL ligand, we report the first example of Cu-mediated enantioselective C–H activation reaction for the construction of planar chiral ferrocenes with high yields and stereoinduction. The key to the success of this reaction is the discovery of a ligand acceleration effect with the BINOL-based diol ligand in the directed Cu-catalyzed C–H alkynylation of ferrocene derivatives bearing an oxazoline-aniline directing group. This transformation is compatible with terminal aryl and alkyl alkynes, which are incompatible with Pd-catalyzed C–H activation reactions. This finding provides an invaluable mechanistic information in determining whether Cu(II) cleaves C–H bonds via CMD pathway in analogous manner to Pd(II) catalysts.
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