Synfacts 2022; 18(05): 0503
DOI: 10.1055/s-0041-1738048
Metals in Synthesis

An Alternative to Norbornene: Unstrained Alkene Ligands with a Coordination Site for Catellani Reactions

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Benedikt Wolff
Zheng Y.-X, Jiao L. * Tsinghua University, Beijing, P. R. of China
Hybrid Cycloolefin Ligands for Palladium–Olefin Cooperative Catalysis.

Nat. Synth. 2022;
1: 180-187
DOI: 10.1038/S44160-021-00019-8
 

Significance

A new ligand design for cooperative palladium–olefin catalysis is disclosed. The combination of an unstrained cycloolefin ligand with a dithiane donor enables palladium-catalyzed Catellani-type reactions with unprecedented reactivity without the need for the norbornene scaffold.


Comment

Various alkyl iodides were employed as coupling partners, demonstrating the broad functional group tolerance of this method. The reaction can be terminated by a Heck reaction or by cross-coupling with organometallic reagents, resulting in vicinal difunctionalization of the aryl iodide.




Publication History

Article published online:
20 April 2022

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