A3‐Coupling Reaction and [Ag(IPr)2]PF6: A Successful Couple. Issue 31 (23rd August 2017)

• Record Type: Journal Article
• Authors: Beillard, Audrey; Métro, Thomas‐Xavier; Bantreil, Xavier; Martinez, Jean; Lamaty, Frédéric
• Is Part Of: European journal of organic chemistry. Issue 31(2017)
• Page Start: 4642
• Page End: 4647
• Publication Date: 2017-08-23
• Subjects: Alkynes -- Amines -- Carbenes -- Silver -- Multicomponent reactions -- Continuous flow; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700985
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The recently described homoleptic cationic [Ag(IPr)2 ]PF6 [IPr = 1, 3‐bis(2, 6‐diisopropylphenyl)imidazolylidene] complex proved to be a versatile and highly efficient catalyst for the production of propargylamines by using the A 3 ‐coupling reaction. The reaction conditions were equally applicable to aliphatic and aromatic aldehydes and alkynes, including highly hindered aromatic aldehydes. Progargylamines were prepared in short reaction times with low catalyst loadings by using MeOH as a low‐toxicity solvent. In addition, the catalyst was stable enough to support continuous‐flow conditions, which showed that the reaction conditions are scalable. Abstract : Homoleptic and cationic [Ag(IPr)2 ]PF6 [IPr = 1, 3‐bis(2, 6‐diisopropylphenyl)imidazolylidene] is an efficient catalyst for the A 3 ‐coupling reaction. Propargylamines are synthesized in short reaction times with low catalyst loadings under microwave irradiation or continuous flow. This approach is user friendly, versatile, and compatible with both aliphatic and aromatic aldehydes and alkynes.