Journal
NATURE COMMUNICATIONS
Volume 13, Issue 1, Pages -Publisher
NATURE PORTFOLIO
DOI: 10.1038/s41467-022-31178-7
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Funding
- Dalian Institute of Chemical Physics [DICPI201902]
- Dalian Outstanding Young Scientific Talent [2020RJ05]
- National Natural Science Foundation of China [22071239]
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This study reports an electrochemically driven method for the efficient synthesis of phosphorylated metallocenes, providing guidance for the C-H functionalization of symmetric metallocenes.
Metallocenes are privileged backbones for synthesis and catalysis. However, the direct dehydrogenative C-H functionalization of unsymmetric metallocenes suffers from reactivity and selectivity issues. Herein, we report an electrochemically driven regioselective C-H phosphorylation of group 8 metallocenes. Mechanistic investigations indicate this dehydrogenative cross coupling occurs through an electrophilic radical substitution of the metallocene with a phosphoryl radical, facilitated by the metallocene itself. This work not only offers an efficient and divergent synthesis of phosphorylated metallocenes, but also provides a guide to interpret the reactivity and regioselectivity for the C-H functionalization of unsymmetric metallocenes. Metallocene-based phosphines are compounds with potential use in catalysis. Here, the authors report the electrochemical regioselective functionalization of group 8 metallocenes with phosphine oxides; over 60 examples of phosphorylated (benzo)ferrocenes and ruthenocenes can be accessed via this method without the need for a preinstalled directing group.
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