2023
DOI: 10.1002/adsc.202300281
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Radical Decyanations of Unactivated Carbon‐CN Bonds: Recent Achievements and Mechanistic Studies

Abstract: Decyanation is an important process in the synthesis of aromatic molecules in the studies of pharmaceutical research, medical and materials sciences. In late‐stage modifications of privileged carbo/heterocyclic scaffolds, radical‐type decyanation techniques have been devised to date. As a result, the chemistry of cyano‐involved conversions, a hotly debated subject over the past few decades, has advanced significantly. The cyano group (CN), on the other hand, has rarely been acknowledged as a good reaction site… Show more

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Cited by 16 publications
(3 citation statements)
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“…In addition to being highly valued building fragments in function materials, dyes, and pharmaceuticals, cyanoarenes can undergo a variety of useful organic transformations . Some advancements in decyanative cross-couplings of cyanoarenes for the formation of carbon–carbon and carbon–heteroatom bonds have been made in recent years .…”
Section: Introductionmentioning
confidence: 99%
“…In addition to being highly valued building fragments in function materials, dyes, and pharmaceuticals, cyanoarenes can undergo a variety of useful organic transformations . Some advancements in decyanative cross-couplings of cyanoarenes for the formation of carbon–carbon and carbon–heteroatom bonds have been made in recent years .…”
Section: Introductionmentioning
confidence: 99%
“…It has been widely used in the decyanative pyridylation reactions for the formation of various C4-functionalized pyridine derivatives. 3–5 For example, the radical–radical cross-coupling of 4-cyanopyridine with diverse radical precursors, 4 the difunctionalization of alkenes such as carbopyridylation, azidopyridylation, pyridylboration, pyridylphosphinoylation, pyridylsilylation and pyridylthiolation were established to give C4-functionalized pyridines. 5 Owing to the great importance of pyridyl-containing structures, developing efficient pyridination methods, especially the incorporation of a pyridyl motif into bioactive molecules, is highly demanded.…”
mentioning
confidence: 99%
“…The in situ generated 1 +• was cleaved to generate benzoyl radical which was soon captured by styrene 2 to afford benzyl radical 6 . Further coupling of 6 with the in situ generated cyanopyridine radical anion 3 –• , affording intermediate 7 which released cyanide to afford β-pyridinyl ketone 4 …”
mentioning
confidence: 99%