Synthesis and reactivity of imidazole-1-sulfonate esters (imidazylates) in substitution, elimination, and metal-catalyzed cross-coupling reactions: a review

Abstract

This review article is an attempt to survey literature describing synthetic methods and reactivity of imidazole-1-sulfonate esters (imidazylates) in substitution, elimination, and metal-catalyzed crosscoupling reactions. N S OR O O N R= alkyl, aryl Synthesis Substitution Elimination Cross-coupling Imidazole-1-sulfonate esters (imidazylates)

Oxime ethers as versatile precursors in organic synthesis: a review

“…This methodology is one of the most useful tools to create new carbon-carbon bonds. 40 In 2013, Medio-Simón et al investigated the Suzuki-Miyaura reaction of achloromethyl oxime ethers 97 with a wide range of boronic acids 98 in the presence of some palladium catalysts. They examined several catalysts and bases, and the system Pd(PPh 3 ) 4 / CsF/THF was found to be superior (Scheme 42).…”

Recent Advances in the Pd‐Catalyzed Coupling of Arylhydrazines and Ammonium Salts via C−N Bond Cleavage

“…Disappointingly, the coupling reactions employing halides as electrophilic partners suffered from drawbacks such as high cost, low reactivity, and toxicity, which limited their industrial application. [9] Although triflates show high reactivity in coupling reactions, they are disadvantaged by their instability and the release of a toxic by-product, triflic acid. Coupling reactions using diazonium salts as electrophilic partners have been a priority area of research, however, their explosiveness and instability are not suitable for synthetic applications.…”

Progress and recent trends in the direct selenocyanation of (hetero)aromatic C–H bonds

“… 11 Traditionally, selenocyanate substituted (hetero)aromatic compounds are obtained through the reaction of selenocyanate sources with active aryl species such as aryl halides, arylboronic acids, and aryl diazonium salt. 12–14 However, toxicity and mutagenicity of organic halides, 15 tedious preparing and purifying arylboronic acids, 16 and high reactivity and instability of diazonium salts 17 may prevent the application of these methods more or less. To overpass these limitations, the direct selenocyanation of (hetero)aromatic C–H bonds has emerged as a powerful and ideal method for the fabrication of (hetero)aryl selenocyanates which because it does not require any pre-functionalized starting materials, offers a more atom economical, greener, and shorter alternative to the classical approaches.…”