CuI in biorenewable basic medium: Three novel and low E-factor Suzuki-Miyaura cross-coupling reactions

• Published in: Molecular catalysis 2022-04, Vol.522, p.112237, Article 112237
• Main Authors: Lakshmidevi, Jangam, Naidu, Bandameeda Ramesh, Venkateswarlu, Katta
• Format: Article
• Language: English
• Subjects: Aqueous medium; CuI; Ligand-free and ligand-assisted conditions; Sustainable Suzuki-Miyaura reaction; Utilization of waste; Water extract of pomegranate ash
• ISSN: 2468-8231; 2468-8231
• DOI: 10.1016/j.mcat.2022.112237

•First use of waste-derived material for Cu-Catalyzed Suzuki-Miyaura coupling.•Utilization of biorenewable waste derived materials.•Actual application of waste to industrially relevant transformation.•Very low E-factor and improved TON and TOF values.•Sustainable synthesis of biaryls using challenging Cu-Catalyst.•Large scope for future investigations.•Ease of handling and wide substrate scope. In this article, we have disclosed three inexpensive and novel copper-catalyzed C(sp2)–C(sp2) coupling reactions of substituted aryl/heteroaryl halides with arylboronic acids by employing water extract of pomegranate ash (WEPA) as biorenewable base and aqueous reaction medium. CuI/WEPA, CuI/WEPA/DABCO, CuI/WEPA/SPhos catalytic systems were developed for the present Suzuki-Miyaura coupling. WEPA has been found to be the effective base and reaction medium for copper-catalysed Suzuki-Miyaura reactions with and without ligands to provide good to high yields of coupling products. This method has remarkable advantages like inexpensive and waste-derived biorenewable base, low catalyst loading, moderate temperature, replacement of precious palladium with abundant copper, no or negligible contamination of copper in products, low E-factor, high chemoselectivity and a large substrate scope. [Display omitted]