http://www.mdpi.com/journal/molecules/special_issues/heck-coupling/ Submission All papers should be submitted to molecules@mdpi.com with copy to the guest editor. To be published continuously until the deadline and papers will be listed together at the special websites. Submitted papers should not have been previously published nor be currently under consideration for publication elsewhere. All papers are refereed through a peer review process. A guide for authors, sample copies and other relevant information for submitting papers are available on the Instructions for Authors page. Molecules is an international peer-reviewed monthly journal published by MDPI. Please visit the Instructions for Authors page before submitting a paper. Article Processing Charges (APC) are 800 CHF per paper and additional English correction fees (250 CHF) will be added in certain cases (1050CHF per paper for those papers that require extensive additional formatting and/or English corrections) for paper submitted before 31 December 2009. Starting 1 January 2010, Article Processing Charges are of 1400 CHF per accepted article for Molecules. http://www.mdpi.com/1420-3049/15/5/3402/ The synthetic potential of stereoselective, palladium-catalyzed hydro(het)arylation reactions of bi-, tri- and tetracyclic (hetero)alkenes in the presence of phospines and arsines as highly efficient ligands was studied. The mechanism of this reductive Heck reaction becomes more complex in the case of benzonorbornenes. Hydroarylation of diazabicyclo-[2.2.1]heptenes provides a stereoselective access to aryldiaminocyclopentanes. Electron-deficient arylpalladium complexes shift the reaction towards the product of a formal 1,2-hydrazidoarylation reaction of 1,3-cyclopentadiene by a stereoselective C-N cleavage. Due to steric reasons, rigid bicyclo[2.2.2]octenes react slower in hydroarylation reactions than the corresponding bicyclo[2.2.1]heptenes. The more flexible bicyclo[4.2.2]decene system already tends to undergo domino-Heck reactions, even under reductive conditions. When a tetracyclic cis-allylcyclopropane is carbopalladated in the presence of formates, the neighboring cyclopropane ring is attacked in the first reported example of a π,σ domino-Heck reaction. http://www.mdpi.com/1420-3049/15/5/3402/ Mon, 10 May 2010 00:00:00 CEST Molecules 2010-05-10 15 5 Review 3402 3410 1420-3049 The Hydroarylation Reaction—Scope and Limitations 2010-05-10 doi: 10.3390/molecules15053402 Namyslo Storsberg Klinge Gärtner Yao Ocal Kaufmann http://www.mdpi.com/1420-3049/15/4/2667/ This review is an overview of the last ten years’ use of the Mizoroki–Heck coupling applied to 1,2- and 1,3-dienes. Since both these systems form π-allyl palladium intermediates in Pd(0) coupling, they show particular chemical behavior. Many examples of 1,2-dienes Heck reactions are presented. 1,2-Dienes are important substrates because of their high reactivity that makes them useful building blocks for the synthesis of biologically relevant structures. http://www.mdpi.com/1420-3049/15/4/2667/ Tue, 13 Apr 2010 00:00:00 CEST Molecules 2010-04-13 15 4 Review 2667 2685 1420-3049 The Heck Reaction Applied to 1,3- and 1,2-Unsaturated Derivatives, a Way towards Molecular Complexity 2010-04-13 doi: 10.3390/molecules15042667 Deagostino Prandi Tabasso Venturello http://www.mdpi.com/1420-3049/15/4/2211/ As the interest for environmental increases and environmental laws become more stringent, the need to replace existing processes with new more sustainable technologies becomes a primary objective. The use of ionic liquids to replace organic solvents in metal catalyzed reactions has recently gained much attention and great progress has been accomplished in this area in the last years. This paper reviews the recent developments in the application of ionic liquids and related systems (supported ionic liquids, ionic polymers, and so on) in the Heck reaction. Merits and achievements of ionic liquids were analyzed and discussed considering the possibility of increasing the effectiveness of industrial processes. http://www.mdpi.com/1420-3049/15/4/2211/ Tue, 30 Mar 2010 00:00:00 CEST Molecules 2010-03-30 15 4 Review 2211 2245 1420-3049 The Heck Reaction in Ionic Liquids: Progress and Challenges 2010-03-30 doi: 10.3390/molecules15042211 Bellina Chiappe http://www.mdpi.com/1420-3049/15/4/2166/ Palladium catalysts containing Pd(II) supported on Al2O3 and alumina-based mixed oxides, Al2O3-ZrO2, Al2O3-CeO2, and Al2O3-Fe2O3, are very effective in the Heck coupling of iodobenzene with cyclohexene in DMF solution. The best results, up to 81% of monoarylated products with a selectivity to 4-phenylcyclohexene (3) close to 90% were obtained with KOH as a base. The catalytic activity of palladium supported on alumina-based oxides was compared with that of homogeneous precursors, such as Pd(OAc)2 and PdCl2(PhCN)2, used in [Bu4N]Br as the reaction medium. Under such conditions homogeneous systems were more selective and produced up to 60% of monoarylated products with a selectivity to 3 close to 60%. http://www.mdpi.com/1420-3049/15/4/2166/ Thu, 25 Mar 2010 00:00:00 CET Molecules 2010-03-25 15 4 Article 2166 2177 1420-3049 Selective Heck Arylation of Cyclohexene with Homogeneous and Heterogeneous Palladium Catalysts 2010-03-25 doi: 10.3390/molecules15042166 Mieczyńska Trzeciak http://www.mdpi.com/1420-3049/15/3/1487/ The direct aerobic coupling reaction of arenes with olefins was successfully achieved by the use of Pd(OAc)2/molybdovanadophosphoric acid (HPMoV) as a key catalyst under 1 atm of dioxygen. This catalytic system could be extended to the coupling reaction of various substituted benzenes with olefins such as acrylates, aclrolein, and ethylene through the direct aromatic C-H bond activation. http://www.mdpi.com/1420-3049/15/3/1487/ Tue, 09 Mar 2010 00:00:00 CET Molecules 2010-03-09 15 3 Review 1487 1500 1420-3049 Pd(II)/HPMoV-Catalyzed Direct Oxidative Coupling Reaction of Benzenes with Olefins 2010-03-09 doi: 10.3390/molecules15031487 Yasushi Obora Yasutaka Ishii http://www.mdpi.com/1420-3049/15/3/1302/ The palladium-catalyzed hydroarylation of N-methyl-substituted tricyclic imides was studied in order to find a new stereoselective access to a series of new exo-aryl(hetaryl)-substituted tricyclic N-methylimides. http://www.mdpi.com/1420-3049/15/3/1302/ Thu, 04 Mar 2010 00:00:00 CET Molecules 2010-03-04 15 3 Article 1302 1308 1420-3049 Reductive Heck Reactions of N-Methyl-substituted Tricyclic Imides 2010-03-04 doi: 10.3390/molecules15031303 Gokce Goksu Nuket Ocal Dieter E. Kaufmann http://www.mdpi.com/1420-3049/15/2/649/ An efficient and stereoselective catalytic system for the Heck cross coupling reaction using novel 1,3-dialkyl-3,4,5,6-tetrahydropyrimidinium salts (1, LHX) and Pd(OAc)2 loading has been reported. The palladium complexes derived from the salts 1a-f prepared in situ exhibit good catalytic activity in the Heck coupling reaction of aryl bromides under mild conditions. http://www.mdpi.com/1420-3049/15/2/649/ Thu, 28 Jan 2010 00:00:00 CET Molecules 2010-01-28 15 2 Article 649 659 1420-3049 Palladium-Catalyzed Heck Coupling Reaction of Aryl Bromides in Aqueous Media Using Tetrahydropyrimidinium Salts as Carbene Ligands 2010-01-28 doi: 10.3390/molecules15020649 Sedat Yaşar Emine Özge Özcan Nevin Gürbüz Bekir Çetinkaya İsmail Özdemir http://www.mdpi.com/1420-3049/15/1/315/ A water-soluble and air-stable Pd(NH3)2Cl2/cationic 2,2’-bipyridyl system was found to be a highly-efficient and reusable catalyst for the coupling of aryl iodides and alkenes in neat water using Bu3N as a base. The reaction was conducted at 140 °C in a sealed tube in air with a catalyst loading as low as 0.0001 mol % for the coupling of activated aryl iodides with butyl and ethyl acrylates, providing the corresponding products in good to excellent yields with very high turnover numbers. In the case of styrene, Mizoroki-Heck coupling products were obtained in good to high yields by using a greater catalyst loading (1 mol %) and TBAB as a phase-transfer agent. After extraction, the residual aqueous solution could be reused several times with only a slight decrease in its activity, making the Mizoroki-Heck reaction “greener”. http://www.mdpi.com/1420-3049/15/1/315/ Tue, 12 Jan 2010 00:00:00 CET Molecules 2010-01-12 15 1 Article 315 330 1420-3049 Palladium(II)/Cationic 2,2’-Bipyridyl System as a Highly Efficient and Reusable Catalyst for the Mizoroki-Heck Reaction in Water 2010-01-12 doi: 10.3390/molecules15010315 Shao-Hsien Huang Jun-Rong Chen Fu-Yu Tsai http://www.mdpi.com/1420-3049/14/8/3019/ The conditions for the C-N bond forming reaction (C-N coupling reaction) between α-bromocarboxylate and nitrogen-containing non-aromatic heterocyclic rings under heterogeneous copper(I) oxide catalysis are investigated in this paper. All the generated compounds were fully characterized by IR, NMR and MS spectroscopy. Ab initio/DFT calculations of partial charges on nitrogen atoms in all the discussed heterocycles and on C(2) of carboxylate under applied conditions were predicted. These in silico results correlate relatively with the experimental observations. http://www.mdpi.com/1420-3049/14/8/3019/ Thu, 13 Aug 2009 00:00:00 CEST Molecules 2009-08-13 14 8 Article 3019 3029 1420-3049 Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles 2009-08-13 doi: 10.3390/molecules14083019 Katerina Brychtova Barbora Slaba Lukas Placek Josef Jampilek Ivan Raich Jozef Csollei