LEADER 05235nam 2200661Ia 450 001 9910830440403321 005 20170809165245.0 010 $a1-282-02242-3 010 $a9786612022425 010 $a0-470-71607-X 010 $a0-470-71606-1 035 $a(CKB)1000000000725025 035 $a(EBL)437539 035 $a(OCoLC)341591179 035 $a(SSID)ssj0000203739 035 $a(PQKBManifestationID)11171115 035 $a(PQKBTitleCode)TC0000203739 035 $a(PQKBWorkID)10174445 035 $a(PQKB)10774867 035 $a(MiAaPQ)EBC437539 035 $a(PPN)242704840 035 $a(EXLCZ)991000000000725025 100 $a20080630d2009 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 04$aThe Mizoroki-Heck reaction$b[electronic resource] /$fedited by Martin Oestreich 210 $aChichester, U.K. $cWiley$d2009 215 $a1 online resource (609 p.) 300 $aDescription based upon print version of record. 311 $a0-470-03394-0 320 $aIncludes bibliographical references and index. 327 $aThe Mizoroki-Heck Reaction; Contents; Foreword; Preface; Contributors; 1 Mechanisms of the Mizoroki-Heck Reaction; 1.1 Introduction; 1.2 Mechanism of the Mizoroki-Heck Reaction when the Catalytic Precursor is Pd(OAc)2 in the Absence of Ligand; 1.3 Mechanism of the Mizoroki-Heck Reaction when the Catalytic Precursor is Pd(OAc)2 Associated with Monophosphine Ligands; 1.3.1 Pd(0) Formation from Pd(OAc)2 in the Presence of a Monophosphine Ligand; 1.3.2 Oxidative Addition; 1.3.2.1 Oxidative Addition of Aryl Iodides; 1.3.2.2 Oxidative Addition of Aryl Triflates 327 $a1.3.3 Complexation/Insertion of the Alkene1.3.4 Multiple Role of the Base; 1.3.5 Catalytic Cycle; 1.3.5.1 Factors Controlling the Efficiency of a Catalytic Reaction; 1.4 Mechanism of the Mizoroki-Heck Reaction when the Catalytic Precursor is Pd(OAc)2 Associated with Bisphosphine Ligands; 1.4.1 Pd(0) Formation from Precursor; 1.4.2 Oxidative Addition; 1.4.3 Complexation/Insertion of the Alkene Regioselectivity; 1.4.4 Catalytic Cycles; 1.5 Mechanism of the Mizoroki-Heck Reaction when the Catalytic Precursor is a P,C-Palladacycle; 1.5.1 Pd(0) Formation from a P,C-Palladacycle 327 $a1.5.2 Catalytic Cycle1.6 Mechanism of the Mizoroki-Heck Reaction when the Ligand is an N-Heterocyclic Carbene; 1.6.1 Oxidative Addition; 1.6.2 Complexation/Insertion of the Alkene; 1.6.3 Catalytic Cycles; 1.7 Mechanism of the Mizoroki-Heck Reaction when the Ligand is a Bulky and Electron-Rich Monophosphine; 1.7.1 Oxidative Addition; 1.7.2 Complexation/Insertion of the Alkene; 1.7.3 Role of the Base in the Recycling of the Pd(0) Complex; 1.7.4 Catalytic Cycle; 1.8 Conclusion; References; 2 Focus on Catalyst Development and Ligand Design; 2.1 Introduction 327 $a2.2 General Considerations: Types of Catalytic System2.2.1 Substrate Dependence; 2.2.2 Ancillary Ligands; 2.2.3 Bases; 2.2.4 Additives; 2.2.5 Media; 2.2.6 Temperature; 2.3 Four Types of Intermolecular Mizoroki-Heck Catalytic System; 2.3.1 The Type 1 Catalytic System; 2.3.2 The Type 2 Catalytic System; 2.3.3 The Type 3 Catalytic System; 2.3.4 The Type 4 Catalytic System; 2.4 Palladium Precatalysts in Type 1 and Type 2 Mizoroki-Heck Reactions; 2.4.1 SRPCs; 2.4.2 Nanoparticles; 2.4.3 Supported Catalysts: Leaching versus Recycling; 2.4.4 Carbene Complexes 327 $a2.4.4.1 N-Heterocyclic Carbene-based Complexes2.4.4.2 N-Heterocyclic Carbene-Based Pincer Complexes; 2.4.4.3 Carbocyclic Carbene-based Complexes; 2.4.5 Palladacycles; 2.4.5.1 C,P-, C,S- and C,N-Palladacycles; 2.4.5.2 Pincer Palladacycles; 2.4.5.3 Palladacycle-Phosphine Complexes; 2.4.6 Nonphosphine Complexes; References; 3 Focus on Regioselectivity and Product Outcome in Organic Synthesis; 3.1 Introduction; 3.2 Mechanistic Aspects; 3.2.1 Oxidative Addition; 3.2.2 -Complex Formation and Migratory Insertion; 3.2.3 -H-Elimination and Palladium(0) Recycling 327 $a3.2.4 Cyclic Alkenes and Double-Bond Migration 330 $aExploring the importance of Richard F. Heck's carbon coupling reaction, this book highlights the subject of the 2010 Nobel Prize in Chemistry for palladium-catalyzed cross couplings in organic synthesis, and includes a foreword from Nobel Prize winner Richard F. Heck. The Mizoroki-Heck reaction is a palladium-catalyzed carbon-carbon bond forming process which is widely used in organic and organometallic synthesis. It has seen increasing use in the past decade as chemists look for strategies enabling the controlled construction of complex carbon skeletons. The Mizoroki-Heck Reaction is 606 $aHeck reaction 606 $aPalladium catalysts 606 $aOrganic compounds$xSynthesis 615 0$aHeck reaction. 615 0$aPalladium catalysts. 615 0$aOrganic compounds$xSynthesis. 676 $a547.2 676 $a547/.2 700 $aOestreich$b Martin$01701154 701 $aOestreich$b Martin$01701154 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910830440403321 996 $aThe Mizoroki-Heck reaction$94084715 997 $aUNINA