The Heck-type arylation of allylic alcohols with arenediazonium salts

Evolution and Synthetic Applications of the Heck–Matsuda Reaction: The Return of Arenediazonium Salts to Prominence

“…In contrast to the investigation reported by Cai et al (not shown), [55] in which only arylated aldehydes were isolated from the same reaction under similar conditions, Muzart and collaborators observed only the formation of acetals 13 and 14. [54] A year later, following the investigations of Roglans and co-workers, Barbero and collaborators explored the application of arenediazonium o-benzenedisulfonimides in the HM arylation of allylic alcohols (Table 14). [56] Once again, secondary allylic alcohols were found to give cleaner reactions, whereas the arylation of primary allylic alcohols was plagued by the formation of mixtures of aldehydes and acetals.…”

Transition metals in organic synthesis: Highlights for the year 2005

“…Both palladium and rhodium were used as catalysts [410]. Tetraarylphosphonium halides [411] and aryl diazonium tetrafluoroborates [412], in a synthesis of rolipram [413] and tosylates and mesylates derived from 1,3-dicarbonyl compounds [414] were used in place of halides and triflates. Halides and triflates of heterocyclic ring systems, such as 3-bromoquinoline-2-ones [177] and 7-bromo-pyrido[2,3-b]pyrazine [185] were used in Heck reactions.…”

Diazotization–cyanation of aromatic amines with crosslinked poly(4‐vinylpyridine)‐supported cyanide ions

“…Aromatic diazonium salts are important building blocks, not only in classical organic synthesis but also in the preparation of modern organic nanocompounds and the grafting of organic molecules onto metallic or nonmetallic surfaces 1–6. Aromatic diazonium salts have gained attention in synthetic chemistry because of their powerful synthetic and industrial importance 7–9. Despite wide applicability in the synthesis of compounds with a diazonium motif, diazonium salts have serious drawbacks: their intrinsic instability and explosive nature.…”