Cu-mediated enantioselective C–H alkynylation of ferrocenes with chiral BINOL ligands

Xin Kuang, Jian-Jun Li, Tao Liu, Chang-Hua Ding, Kevin Wu, Peng Wang () and Jin-Quan Yu ()
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Xin Kuang: Shanghai Institute of Organic Chemistry
Jian-Jun Li: Shanghai Institute of Organic Chemistry
Tao Liu: Shanghai Institute of Organic Chemistry
Chang-Hua Ding: Shanghai University
Kevin Wu: The Scripps Research Institute (TSRI)
Peng Wang: Shanghai Institute of Organic Chemistry
Jin-Quan Yu: The Scripps Research Institute (TSRI)

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-023-43278-z

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