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Synfacts 2023; 19(08): 0773
DOI: 10.1055/s-0042-1752836
DOI: 10.1055/s-0042-1752836
Metals in Synthesis
The Catellani Reaction meets C–H Activation: Synthesis of 1,3-Disubstituted Planar Chiral Metallocenes
Zhou L,
Cheng H.-G,
*,
Li L,
Wu K,
Hou J,
Jiao C,
Deng S,
Liu Z,
Yu J.-Q,
*,
Zhou Q.
*
Wuhan University and Nankai University, Tianjin, P. R. of China; The Scripps Research
Institute, La Jolla, USA
Synthesis of Planar Chiral Ferrocenes via Enantioselective Remote C–H Activation.
Nat. Chem. 2023;
15: 815-823
DOI: 10.1038/s41557-023-01176-3
Synthesis of Planar Chiral Ferrocenes via Enantioselective Remote C–H Activation.
Nat. Chem. 2023;
15: 815-823
DOI: 10.1038/s41557-023-01176-3
Key words
Catellani reaction - palladium catalysis - planar chiral metallocenes - remote C–H activation
Significance
The synthesis of planar 1,3-disubstituted chiral metallocenes via palladium-catalyzed remote C–H activation is reported. The reaction features high enantioselectivities and good functional group tolerance. Aryl iodides as well as bromides serve as compatible coupling partners.
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Comment
An initial directed enantiodetermining C–H activation at the ortho-position, enabled by a chiral mono-N-protected natural amino acid ligand, is followed by a C–H activation of the remote meta-position using a bridgehead-substituted norbornene mediator, akin to the Catellani reaction.
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Publication History
Article published online:
14 July 2023
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