Copper‐Catalyzed Base‐free Protocol for the Sonogashira‐type Coupling of Phenylacetylenes with Boronic Acid Derivatives under Air. Issue 31 (18th August 2022)

• Record Type: Journal Article
• Authors: Saranya, Salim; Saranya, Padinjare Veetil; Anilkumar, Gopinathan
• Is Part Of: ChemistrySelect. Volume 7:Issue 31(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-18
• Subjects: Acetylenes -- Boronic acid -- Copper -- Coupling -- Internal alkynes -- Sonogashira reaction; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202202191
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A base‐free Cu‐catalyzed protocol for the synthesis of internal alkynes using phenylacetylenes and boronic acid derivatives has been developed. We have used the less expensive catalyst CuI in greener solvent methanol using air as oxidant for the synthesis of diarylacetylenes. The methodology furnished the diarylacetylene derivatives in moderate to excellent yields. Abstract : A novel methodology on C−C coupling of acetylenes with boronic acids was developed. The new strategy involves the mild reaction condition of 10 mol% CuI and 10 mol% 1, 10‐phenanthroline in methanol at RT in an open vessel. The generality of the reaction was studied using a wide range of boronic acids. A possible mechanistic rationale was also proposed.