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Synfacts 2023; 19(08): 0773
DOI: 10.1055/s-0042-1752836
Metals in Synthesis

The Catellani Reaction meets C–H Activation: Synthesis of 1,3-Disubstituted Planar Chiral Metallocenes

Rezensent(en):
Martin Oestreich
,
Hendrik F. T. Klare
,
Aliyaah J. M. Rahman
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
CrossrefPubMedSuche in Google Scholar
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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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Publikationsverlauf

Artikel online veröffentlicht:
14. Juli 2023

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