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      An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

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          Abstract

          Aqueous Mizoroki–Heck coupling reactions under microwave irradiation (MW) were carried out with a colloidal Pd nanocatalyst stabilized with poly( N-vinylpyrrolidone) (PVP). Many stilbenes and novel heterostilbenes were achieved in good to excellent yields starting from aryl bromides and different olefins. The reaction was carried out in a short reaction time and with low catalyst loading, leading to high turnover frequency (TOFs of the order of 100 h −1). The advantages like operational simplicity, high robustness, efficiency and turnover frequency, the utilization of aqueous media and simple product work-up make this protocol a great option for stilbene syntheses by Mizoroki–Heck reaction.

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          Most cited references64

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          The heck reaction as a sharpening stone of palladium catalysis.

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            Intermolecular dehydrogenative Heck reactions.

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              Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: a unifying view.

              Pd catalysis of C-C bond formations is briefly reviewed from the angle of nanoparticles (NPs) whether they are homogeneous or heterogeneous precatalysts and whether they are intentionally preformed or generated from a Pd derivative such as Pd(OAc)2. The most studied reaction is the Heck coupling of halogenoarenes with olefins that usually proceeds at high temperature (120-160 degrees C). Under such conditions, the PdII precursor is reduced to Pd0, forming PdNPs from which Pd atom leaching, subsequent to oxidative addition of the aryl halide onto the PdNP surface, is the source of very active molecular catalysts. Other C-C coupling reactions (Suzuki, Sonogashira, Stille, Negishi, Hiyama, Corriu-Kumada, Ullmann, and Tsuji-Trost) can also be catalyzed by species produced from preformed PdNPs. For catalysis of these reactions, leaching of active Pd atoms from the PdNPs may also provide a viable molecular mechanistic scheme. Thus, the term "PdNP catalysis of C-C coupling" used in this review refers to this function of PdNPs as precursors of catalytically active Pd species (i.e., the PdNPs are precatalysts of C-C coupling reactions).
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                Author and article information

                Contributors
                Role: Associate Editor
                Journal
                Beilstein J Org Chem
                Beilstein J Org Chem
                Beilstein Journal of Organic Chemistry
                Beilstein-Institut (Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany )
                1860-5397
                2017
                18 August 2017
                : 13
                : 1717-1727
                Affiliations
                [1 ]INFIQC-CONICET- Universidad Nacional de Córdoba, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Haya de la Torre y Medina Allende, Ciudad Universitaria, X5000HUA, Córdoba, Argentina
                Article
                10.3762/bjoc.13.166
                5564268
                28904615
                6c2a2a21-3f54-42bf-b4fb-d74604a026c0
                Copyright © 2017, García et al.; licensee Beilstein-Institut.

                This is an Open Access article under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: ( http://www.beilstein-journals.org/bjoc)

                History
                : 25 April 2017
                : 4 August 2017
                Categories
                Full Research Paper
                Chemistry
                Organic Chemistry

                Organic & Biomolecular chemistry
                aqueous reaction medium,maos,mizoroki–heck reaction,pd nanoparticle,sustainable organic synthesis

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