Cobalt-Catalyzed Decarboxylative Allylations: Development and Mechanistic Studies.

Chemistry

Department of Chemistry, The University of Kansas, 1567 Irving Rd., Lawrence, KS 66045, USA.

Published: October 2023

In recent years, there has been a concerted drive to develop methods that are greener and more sustainable. Being an earth-abundant transition metal, cobalt offers an attractive substitute for commonly employed precious metal catalysts, though reactions engaging cobalt are still less developed. Herein, we report a method to achieve the decarboxylative allylation of nitrophenyl alkanes, nitroalkanes, and ketones employing cobalt. The reaction allows for the formation of various substituted allylated products in moderate-excellent yields with a broad scope. Additionally, the synthetic potential of the methodology is demonstrated by the transformation of products into versatile heterocyclic motifs. Mechanistic studies revealed an in situ activation of the Co(II)/dppBz precatalyst by the carboxylate salt to generate a Co(I)-species, which is presumed to be the active catalyst.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10592299PMC
http://dx.doi.org/10.1002/chem.202302174DOI Listing

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