Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones. Issue 34 (22nd August 2018)

• Record Type: Journal Article
• Authors: Charugandla, Renuka; Vangala, Markandeya Sarma; Chidara, Sridhar; Korupolu, Raghu Babu
• Is Part Of: Tetrahedron letters. Volume 59:Issue 34(2018)
• Page Start: 3283
• Page End: 3287
• Publication Date: 2018-08-22
• Subjects: Ni(OAc)2 catalyzed carbonylative Sonogashira reaction -- Aryl α, β-alkynyl ketones -- 2-Substituted flavones -- Palladium/phosphine free conditions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.07.042
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Ligand free Nickel Catalyzed Carbonylative Sonogashira was developed. Various α, β-alkynyl ketones and flavones synthesized. Economically liable method to synthesise the substituted and heteroaromatic alkynyl ketones. Abstract: The nickel catalyzed, palladium/phosphine free carbonylative Sonogashira reaction of terminal alkynes with substituted aryl and heteroaryl iodides is described. This protocol provides mild and robust conditions to synthesize a variety of substituted aryl α, β-alkynyl ketones and flavones in good to excellent isolated yields. This methodology tolerates several functional groups such as electron donating (methyl, isopropyl, tert -butyl, methoxy) as well as electron withdrawing (trifluoromethyl, nitro, esters, nitrile) groups on the terminal alkynes and iodides.