Metal-Free, Oxidative Condensation of Heteroaryl- and Aryl Carbaldehydes towards Functionalized Carbonitriles

Agyei, Eric A.; Carrick, Jesse D.

doi:10.1002/slct.202300866

Metal-Free, Oxidative Condensation of Heteroaryl- and Aryl Carbaldehydes towards Functionalized Carbonitriles

Journal Article · Mon Jun 19 00:00:00 EDT 2023 · Chemistry Select

DOI:https://doi.org/10.1002/slct.202300866· OSTI ID:2420690

Agyei, Eric A. ^[1]; ^[2]

Tennessee Technological Univ., Cookeville, TN (United States); OSTI
Tennessee Technological Univ., Cookeville, TN (United States)

Functionalization of pyridines with the carbonitrile group for advanced cyclization reactions routinely incorporates metals, toxic oxidants, and cyanide reagents, often in linear synthetic sequences. Here, motivated by the strategic need of a heteroaryl carbonitrile synthon for further elaboration, we disclose an efficient, metal-free, one-pot reaction sequence that uses ammonium acetate as the nitrogen source and bis-acetoxyiodobenzene as the oxidant with low loadings. The developed method tolerates a diverse substrate scope including heteroaryl, aryl, and alkyl substrates with similar efficiency and expands the practitioner's reaction. Method development, optimization, substrate scope, preliminary mechanistic observations, competition experiments, and a scale up reaction are delineated herein.

View Accepted Manuscript (DOE)

Research Organization:: Tennessee Technological Univ., Cookeville, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0018033

OSTI ID:: 2420690

Journal Information:: Chemistry Select, Journal Name: Chemistry Select Journal Issue: 23 Vol. 8; ISSN 2365-6549

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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