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Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive
Author(s) -
Prabhala Pavankumar,
Savanur Hemantkumar M.,
Kalkhambkar Rajesh G.,
Laali Kenneth K.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900093
Subject(s) - chemistry , sonogashira coupling , ligand (biochemistry) , combinatorial chemistry , piperidine , solvent , scope (computer science) , organic chemistry , catalysis , receptor , palladium , computer science , biochemistry , programming language
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][NTf 2 ] 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.