Water extract of pomegranate ash (WEPA), an agro waste (bio) derived novel and sustainable medium, has been developed for the Ullmann coupling of aryl halides under added base, ligand and reducing agent free palladium catalysis in open-air.
Ac onvenient and efficient palladium(II)-porphyrin catalytic system has been developed for the Suzuki-Miyaura cross-coupling (SMC) of aryl bromides with potassium aryltrifluoroborate in water.Aseries of seven different porphyrins and their complexes with palladium (Pd II (por)-1-Pd II (por)-7) were prepared, and screenedt heir catalytic activity in making biaryls through C(sp 2 )ÀC(sp 2 )c oupling.S ignificantly, the present protocol utilizes safe, water-soluble, and highly stable porphyrins as an alternative to toxic and unstable phosphine ligands. Thes imple preparation of porphyrins and their complexes, use of moisture-resistantc atalyst, excellent yields of the isolated products,u se of eco-friendly solvent( such as water), and reusability of the catalysta re the notable advantages of this method. This finding uses marginally explored, moisture-insensitive potassium phenyltrifluoroborates as nucleophilesf or SMC. Furthermore, the scope of the methodh as been demonstrated for the multigram scale preparation of biaryls without any side products.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.
A facile palladium(II)‐porphyrin catalytic system has been developed for the Mizoroki‐Heck coupling of aryl bromides with alkyl acrylates under mild conditions. Seven different porphyrins (H2TPP, H2TpCPP, H2TpAP, H2TpTP, H2TSTpSPP, H2TmHPP and H2TmCPP) and their complexes with palladium (Pd‐TPP, Pd‐TpCPP, Pd‐TpAP, Pd‐TpTP, Pd‐TSTpSPP, Pd‐TmHPP and Pd‐TmCPP) were synthesized, and examined their catalytic role in the synthesis of alkyl cinnamates in DMF. The complex, Pd‐TSTpSPP showed better activity in the present conversion. This finding has significant advantages like operational simplicity, easy synthesis of porphyrin ligands and their complexes with palladium, utilization of safer and recyclable catalyst and high yields of Mizoroki‐Heck products.
An agro waste‐derived, ‘water extract of pomegranate ash’ (WEPA), has been utilized for the first time as a renewable medium for Pd(OAc)2‐catalysed Suzuki–Miyaura cross‐coupling at room temperature. This method offers a simple and sustainable synthesis of biaryls from aryl halides and arylboronic acids under ligand‐ and external base‐free aerobic and ambient conditions. This method has been found effective for both activated and unactivated aryl halides in the production of biaryls with moderate to nearly quantitative yields. The protocol shows high chemoselectivity over identical/similar reactive sites in aryl halides (i.e. selectivity over identical halogens or different halogens of aryl halides). This method exhibits high regioselectivity, i.e. the selective reactivity of a halogen over other identical halogens at different positions on the aromatic nucleus. Therefore, we disclose here a clean, benign, substantial chemo‐ and regioselective and highly economic alternative method for the palladium‐assisted synthesis of biaryls using an agro waste‐derived medium.
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