Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive. Issue 10 (3rd March 2019)

• Record Type: Journal Article
• Authors: Prabhala, Pavankumar; Savanur, Hemantkumar M.; Kalkhambkar, Rajesh G.; Laali, Kenneth K.
• Is Part Of: European journal of organic chemistry. Issue 10(2019)
• Page Start: 2061
• Page End: 2064
• Publication Date: 2019-03-03
• Subjects: Decarboxylative Sonogashira -- Carboxylic acids -- Iododediazoniation -- Alkynes -- Imidazolium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900093
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : A facile one‐pot method comprising sequential iododediazoniation/Sonogashira reaction is used to prepare diverse libraries of internal alkynes. The method uses imidazolium‐ILs as base and solvent and does not require ligand or additive.