Facile synthesis of aryl-substituted pyridines via Suzuki–Miyaura approach

Zinc Chloride Mediated Synthesis of 1,4‐Oxazepines from N‐Propargylic β‐Enaminones

“…In this regard, we have recently shown that when treated with molecular iodine in the presence of sodium hydrogen carbonate, N ‐propargylic β‐enaminones undergo electrophilic cyclization to afford iodo‐substituted pyridines in good to high yields with a broad range of functional group tolerance . Iodopyridines have been further elaborated to more complex structures by metal‐catalyzed coupling reactions such as Suzuki–Miyaura and Sonogashira reactions . We anticipate that other metal Lewis acids, particularly inexpensive ones, could affect the intramolecular cyclization of N ‐propargylic β‐enaminones to generate seven‐membered ring systems.…”

Exploiting C–H borylation for the multidirectional elaboration of 2-halopyridines

“…As such, methods to synthesise functionalised pyridines are of great value and much effort has been applied towards this effect. [5][6][7][8][9][10][11] Given the low reactivity of the electron deficient azinyl ring towards electrophilic aromatic substitution, most routes to substituted pyridines involve de novo synthesis with substituents and substitution patterns determined by the building blocks employed. However, the ability to manipulate a preformed pyridine ring is particularly valuable for late stage diversification.…”

N-Propargylic β-enaminocarbonyls: powerful and versatile building blocks in organic synthesis

“…17 Subsequently, the above cyclization products, applied by the same authors to the synthesis of more functionalized pyridines via transition metalcatalyzed processes, such as Sonogashira and Suzuki-Miyaura cross-coupling reactions. 18,19 Recently, Cheng et al developed a simple and efficient methodology for the synthesis of 2-(1-heteroaryl) pyridines 38 by the reaction between 1,3-diphenyl-3-(prop-2-ynylamino)prop-2en-1-one 36 and N-heteroarenes 37 (Scheme 16). 20 NaOH was the most efficient catalyst among the bases such as LiO t Bu, NaO t Bu, K 2 CO 3 , KOH, Et 3 N etc for this reaction.…”