Cobalt‐Catalyzed Carbonylations

Volkman, Jérôme; Kalck, Philippe

doi:10.1002/9783527829354.ch2

Cited by 1 publication

(1 citation statement)

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“…To avoid the use of an expensive noble metal catalyst system, we began to evaluate our idea by using more abundant and comparably inexpensive cobalt catalysts. , As a benchmark reaction, the carbonylation of N-(butenyl)-benzamide 2s with perfluorobutyl iodide and CO (40 bar) was examined in the presence of Co(acac) 2 and various nitrogen and phosphorus ligands at 120 °C. Notably, in this model system, the acylation of the less reactive amide bond should be facilitated because of the intramolecular ring closure reaction.…”

Section: Resultsmentioning

confidence: 99%

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

Wang

Neumann

et al. 2023

ACS Catal.

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A general and broadly applicable cobalt-catalyzed multicomponent 1,2-perfluoroalkylation carbonylation of alkenes has been developed. This protocol allows the synthesis of β-perfluoroalkyl-substituted amides, esters, and related derivatives using olefins, carbon monoxide, commercially accessible perfluoroalkyl iodides, and a variety of nucleophiles including low nucleophilic amides and urea derivatives in a one-pot manner. As an example, readily available trifluoroiodomethane can be utilized forming pharmaceutically relevant β-trifluoromethylated amides. To showcase the application potential, the perfluoroalkylation carbonylation process was applied to selected current drugs and biologically active molecules. The methodology permits a straightforward increase of the molecular complexity of olefins toward functionalized perfluoroalkylated building blocks in a regioselective manner.

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Section: Resultsmentioning

confidence: 99%