Special Issue "Suzuki Reaction"

Guest Editor
Prof. Dr. Anna Trzeciak
Faculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie Str., 50-383 Wrocław, Poland
E-Mail: anna.trzeciak@chem.uni.wroc.pl
Interests: coordination and organometallic chemistry; homogeneous and heterogenized metal complex catalysis; nanocatalysis; mechanistic studies of hydroformylation; palladium catalyzed C-C cross-coupling and carbonylation reactions; polymerization of phenylacetylene

Dear Colleagues,

Suzuki reaction presents one of the most useful methodologies applied for the synthesis of unsymmetrical biaryls, which are important components for pharmaceutical agents, organic materials and natural products.  Palladium compounds and palladium nanoparticles are today considered as the most active catalysts of Suzuki reaction, however there are also reports indicating on the possibility of successful application of other metals in this process. Moreover, improvement of reaction conditions to more environmentally friendly has been a highly topical field of study.
The aim of this special issue is to present the most actual trends in the area of Suzuki reaction.
Contributions for this issue, both in form of original research and review articles, may cover all aspects of Suzuki reaction e.g. application of Suzuki methodology for the synthesis of functionalized organic molecules and compounds of potential biological activity, new catalysts presenting high activity and selectivity, homogeneous, immobilized and heterogeneous catalysts for the Suzuki reaction, improvement of Suzuki reaction conditions by application of alternative energy sources and green solvents, mechanistic studies and identification of catalytically active species, asymmetric Suzuki reaction, Suzuki reaction as a part of tandem processes.

Prof. Dr. Anna Trzeciak
Guest Editor

Submission

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• cross-coupling reactions
• boronic acids
• selectivity
• functionalized biphenyls
• homogeneous catalysts
• heterogeneous catalysts
• palladium
• palladium nanoparticles
• reaction mechanism
• reaction media
• asymmetric Suzuki reaction

Type of Paper: Review
Title: The Suzuki Reaction — The Versatile Method for the Introduction of New C–C Bonds
Authors: Jadwiga Sołoducho, Kamila Olech, Dorota Zając and Joanna Cabaj
Affiliation: Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Abstract: Over the past 10 years, small molecule solid phase synthesis has become a powerful tool in the discovery of in example new drugs or molecular materials. In the development of organic chemistry, the carbon–carbon bond formation has always been one of the most useful and fundamental reaction. According to fact, the current researches summarize recent developments in metal-catalyzed coupling reactions.
The following methods are investigated in details: the cross-coupling of aryl halides with aryl boronic acids (the Suzuki coupling); the palladium-catalyzed reaction between an aryl and (or) alkyl halide and a vinyl functionality (the Heck reaction); and the palladium-catalyzed cross-coupling reaction of organostannyl reagents with a variety of organic electrophiles (the Stille reaction).
Organic transformations in aqueous media have received also much attention because water is mainly harmless to the environment. The cross-coupling reaction of alkenyl and aryl halides with organoborane derivatives in the presence of a palladium catalyst and a base (Suzuki reaction) has often been carried out in an organic–aqueous mixed solvent. Although Davidson and Triggs discovered in 1968 that arylboronic acids reacted with palladium(II) acetate to give corresponding biaryls, and Garves in 1970 that arylsulfinic acids could be coupled to biaryls using Pd(II) in aqueous solvents, it was not until 1979 when biaryls could efficiently be prepared by a palladium- catalyzed reaction. Miyaura and Suzuki reported that cross-coupling reactions between alkenylboranes and organic halides were efficiently catalyzed by a catalytic amount of tetrakis(triphenylphoshine) palladium (Pd(PPh3)4) in the presence of a suitable base.
In this contents, using the conventional bridged derivatives (phenoxazine, phenothiazine, fluorene, carbazole as a functional segments) the palladium catalyzed condensation halide arylenes by Suzuki-, and other coupling reactions were used as well-established procedure in modern organic synthesis. The coupling products find good applications as intermediates in the preparation of materials. However, the Suzuki- type reactions catalyzed by heterogeneous palladium involving bromoarenes are relatively unexplored. In this context, polymer-supported catalysts have become valuable tools offering many advantages such as simplification of product synthesis.
We report also some example of the photophysical and sensor properties of the thin films built of synthesized copolymers and their electrochemical character.
This current review summarizes recent developments in Suzuki type, palladium-catalyzed coupling reactions. This short review summarizes the advantages of using the Suzuki protocol instead of other similar cross-coupling reactions, several structurally different ligands that promote the reaction in water, recent results from ligandless Suzuki procedure, and target molecules mainly produced by the method.

Type of paper: Review
Title: Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments
Authors: Cristina Prandi, Hèlena Rosso, Marco Blangetti and Paolo Venturello
Affiliation: Università di Torino, Dipartimento di Chimica, via P. Giuria 7 10125 Torino, Italy
Abstract: Since the first report and due to its handiness and wide scope, the Suzuki cross coupling reaction has become a routine methodology in many laboratories worldwide.With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the carbonylative SM coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis.