Rapid Access to Multisubstituted Acrylamides from Cyclic Ketones via Palladium/Norbornene Cooperative Catalysis.

Zhao Wu, Guangbin Dong

Angewandte Chemie (International ed. in English) 2022 Apr 19

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A strategy to access diverse multisubstituted acrylamides from cyclic ketones is realized via palladium/norbornene-catalyzed α-carbamoylation and ipso-functionalization of the corresponding enol triflates. The development of bulky C2 secondary amide-substituted norbornene cocatalysts is the key to achieve the desired reactivity and selectivity. Readily available carbamoyl chlorides serve as effective electrophiles; various moieties including alkenyl, hydrogen, alkynyl, aryl, and alkyl groups can be installed at the ipso position. In addition, tandem α-carbamoylation/ipso-annulations are demonstrated to furnish lactam-containing polycyclic scaffolds. The utility of this method is exemplified in the streamlined preparation of a platelet-activating factor (PAF)-antagonist. © 2022 Wiley-VCH GmbH.

Citation

Zhao Wu, Guangbin Dong. Rapid Access to Multisubstituted Acrylamides from Cyclic Ketones via Palladium/Norbornene Cooperative Catalysis. Angewandte Chemie (International ed. in English). 2022 Apr 19;61(17):e202201239