Porphyrin N-Pincer Pd(II)-Complexes in Water: A Base-Free and Nature-Inspired Protocol for the Oxidative Self-Coupling of Potassium Aryltrifluoroborates in Open-Air

Molecules

Sivarama Krishna Lakkaboyana¹  Ravi Kumar Marella²  Marlia M. Hanafiah³  Sana Siva Prasad⁴  Jangam Lakshmidevi⁴  Katta Venkateswarlu⁴  Bandameeda Ramesh Naidu⁴ 

[1] Department of Chemical Technology, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand;Department of Chemistry, PACE Institute of Technology & Sciences, Ongole 523272, India;Department of Earth Sciences and Environment, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi 43600, Selangor, Malaysia;Laboratory for Synthetic & Natural Products Chemistry, Department of Chemistry, Yogi Vemana University, Kadapa 516005, India;

关键词: porphyrin N-pincer Pd(II)-complexes;    water;    nature-inspired conditions;    potassium aryltrifluoroborates;    self-coupling;    symmetrical biaryls;   

DOI  :  10.3390/molecules26175390

来源: DOAJ

【 摘 要 】

Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.

【 授权许可】

Unknown