1‐Aryltriazenes, the protected and more stable form of aryl‐diazonium species, can be conveniently unmasked with Brønsted acidic‐IL or Sc(OTf)3 and coupled with a host of aryl/heteroaryl boronic acids, styrenes, and aryl/alkyl acetylenes in the Suzuki, Heck and Sonogashira reactions in one‐pot and in respectable isolated yields, by using palladium or nickel catalyst in readily available imidazolium ILs as solvent, under mild conditions. The scope of these reactions are explored, and the potential for recovery/reuse of the IL solvent is also addressed.

A green C−H bond activation of azole based bio‐pertinent substrates such as benzoxazole, benzothiazole, benzimidazole are accomplished using readily prepared 1‐aryltriazenes as arylating agent. Under an optimized condition employing Pd(OAc)2 and CuI in either hydrophilic [Bmim][BF4] or hydrophobic [Bmim][PF6] IL medium with [BMIM(SO3H)][OTf] as a promoter, these arylation reactions proceeded smoothly to afford 2‐aryl substituted azoles in acceptable to better yields besides noticeable functional group tolerance. The prospective for recovery and re‐use of ionic liquid solvent is demonstrated.

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Convenient access to diverse libraries of internal alkynes via decarboxylative Sonogashira reaction of alkynyl‐carboxylic acids with iodoarenes, employing imidazolium‐ILs as solvent, along with piperidine‐appended imidazolium [PAIM][NTf2] as task‐specific basic IL is demonstrated, without the need for any ligand or additive. The feasibility to perform these reactions by sequential one‐pot iododediazoniation/decarboxylative Sonogashira reaction is also shown, and the scope of the methods is underscored by providing 29 examples. The potential for recycling and reuse of the IL solvent is also examined.

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