Metal-catalyzed Cross-coupling Reactions

Автор(ы):Diedreich F., Stang P. J.
06.10.2007
Год изд.:1998
Описание: Metal-catalyzed cross-coupling reactions are extensively employed in a wide range of areas of preparative organic chemistry, from the synthesis of complex natural products to supramolecular chemistry and materials science. For example, the formation of new carbon-rich polymers and networks by acetylenic molecular scaffolding, the development of many abiotic receptors, and the preparation of many dendrimers depends heavily on modern cross-coupling methodologies. In fact, in the 1990s one can hardly open a chemical journal in the broad area of organic chemistry or materials science that does not contain several examples of cross-coupling reactions.
Оглавление:
Metal-catalyzed Cross-coupling Reactions — обложка книги. Обложка книги.
1 Palladium- or Nickel-catalyzed Cross-coupling with Organometals Containing Zinc, Magnesium, Aluminum, and Zirconium Ei-ichi Negishi, Fang Liu
  1.1 Introduction [1]
  1.2 Systematic survey of palladium-or nickel-catalyzed cross-coupling [4]
    1.2.1 Scope with respect to metal counterions and inhibition of catalysis by organolithiums [4]
    1.2.2 Cross-coupling between two unsaturated carbon groups [6]
      1.2.2.1 Palladium-catalyzed cross-coupling involving alkynylmetals and related alkynyl nucleophiles: alkynyl-aryl, alkynyl-alkenyl, and alkynyl-alkynyl coupling [6]
      1.2.2.2 Hydrometallation cross-coupling and carbometallation — cross-coupling tandem protocols and other alkenyl-aryl, alkenyl-alkenyl, and alkenyl-alkynyl coupling reactions: double metal catalysis [7]
      1.2.2.3 Aryl-aryl coupling [10]
    1.2.3 Palladium-catalyzed cross-coupling involving alkyl groups without proximal unsaturation [12]
    1.2.4 Cross-coupling involving allyl, benzyl, and propargyl groups [16]
      1.2.4.1 Coupling reactions of alkenyl- and arylmetals with allyl, benzyl, and propargyl electrophiles [16]
      1.2.4.2 Cross-coupling with allyl-and benzylmetals [18]
    1.2.5 Cross-coupling involving carbonyl compounds [18]
      1.2.5.1 Palladium-catalyzed acylation of organometals with асуl halides [18]
      1.2.5.2 Palladium-catalyzed allylation and related reactions of enolates [19]
      1.2.5.3 (?)-Substitution of carbonyl compounds with unsaturated carbon groups [21]
    1.2.6 Leaving groups [24]
    1.2.7 Ligands [26]
  1.3 Assymetric cross-coupling [27]
  1.4 Palladium-catalyzed tandem processes involving cross-coupling reactions [30]
  1.5 Mechanism of cross-coupling [34]
  1.6 Conclusions [37]
  1.7 Representative experimental procedures [39]
    1.7.1 (?)-Methoxyphenylethyne [39]
      1.7.1.1 Preparation of ethynylzinc chloride [39]
      1.7.1.2 Preparation of (?)methoxyphenylethyne [39]
    1.7.2 (7E,9E,11E,13E)-Retinol (vitamin A) [40]
    1.7.3 (?)-Farnesene [41]
    1.7.4 (Z)-1-[1(?)-methyl-(E)-2'-heptenylidene]indan [41]
  Abbreviations [42]
  References [42]
2 Cross-coupling Reactions of Organoboron Compounds with Organic Halides Akira Suzuki
  2.1 Introduction [49]
  2.2 Preparation of organoboron compounds [49]
    2.2.1 Hydroboration of alkenes and alkynes [49]
    2.2.2 Haloboration of terminal alkynes [51]
    2.2.3 Preparation from organolithium and magnesium reagents [52]
    2.2.4 Miscellaneous methods [53]
  2.3 Palladium-catalyzed reactions of organoboron compounds and their mechanism [54]
    2.3.1 Cross-coupling reactions [54]
    2.3.2 Other reactions catalyzed by transition-metal complexes [61]
  2.4 Cross-coupling reactions of organoboron compounds [63]
    2.4.1 Coupling of 1-alkenylboron derivatives: Synthesis of conjugated dienes [63]
    2.4.2 Coupling of arylboron compounds: Synthesis of biaryls [70]
    2.4.3 Coupling of alkyboron derivatives [74]
    2.4.4 Reactions with Inflates [79]
    2.4.5 Carbonylative coupling [81]
  2.5 Conclusions [82]
  2.6 Experimental procedures [84]
    2.6.1 Reaction of 1-alkenylboronates with vinylic halides: Synthesis of (1Z, 3E)-1-phenyl-1,3-octadiene [84]
    2.6.1.1 (E)-1-Hexenyl-1,3,2-benzodioxaborole [84]
    2.6.1.2 (IZ, 3E)-1-Phenyl-1,3-octadiene [85]
    2.6.2 Reaction of arylboronic acids with haloarenes: synthesis of sterically hindered biaryls [85]
    2.6.3 Reaction of 9-alkyl-9-borabicyclo[3.3.1]nonane with 1-bromo-1-phenylthioethene: synthesis of 4-(3-cyclohexenyl)-2-phenylthio-1-butene [86]
      2.6.3.1 1-Bromo-1-phenylthioethene [86]
      2.6.3.2 9-[2-(3-Cyclohexenyl)ethylJ-9-BBN [86]
      2.6.3.3 4-(3-Cyclohexenyl)-3-phenylethio-1-butene [87]
    2.6.4 Intramolecular cross-coupling of enol inflates with organoboron compounds: Synthesis of 2,3-trimethylene-3-carbomethoxycycloheptene [88]
      2.6.4.1 2-Allyl-2-carbomethoxycyclo-7-heptenyl triflate [88]
      2.6.4.2 2,3-Trimethylene-3-carbomethoxycyclo-7-heptene [88]
    2.6.5 Carbonylative coupling reaction: Synthesis of (?)-5-pentadecen-7-one [88]
  Abbreviations [89]
  References [89]
3 Palladium-catalyzed Coupling of Organyl Halides to Alkenes - The Heck Reaction Stefan Brase, Arrnin de Meijere
  3.1 Introduction [99]
  3.2 Principles [99]
    3.2.1 The mechanism [99]
    3.2.2 The catalysts [101]
    3.2.3 Thealkenes [102]
    3.2.4 Effects of bases, ligands, and additives [105]
    3.2.5 The leaving groups [107]
    3.2.6 Stereochemical requirements in intramolecular cyclizations [112]
  3.3 Cascade reactions and multiple couplings [114]
    3.3.1 Heck cascades involving sp2 centers [115]
    3.3.2 Heck-reaction cascades involving sp2 and sp centers [116]
    3.3.3 Cascades consisting of Heck and subsequent cycloaddition or electrocyclization reactions [117]
      3.3.3.1 Heck and Diels-Alder cascades [117]
      3.3.3.2 Heck блг-electrocyclization cascades [118]
    3.3.4 Heck combined with other cross-coupling processes [121]
    3.3.5 Palladium-catalyzed reactions with nucleophilic substrates [122]
    3.3.6 Heck-aldol and Heck-Michael cascades [126]
    3.3.7 С—H activation in Heck-type processes [127]
    3.3.8 Heck with consecutive carbonylation reactions [130]
    3.3.9 Multiple Heck couplings [130]
  3.4 Related palladium-catalyzed reactions [133]
  3.5 Enantioselective Heck-type reactions [134]
  3.6 Syntheses of natural products and biologically active compounds [139]
  3.7 Conclusions [141]
  3.8 Experimental procedures [148]
    3.8.1 Dipotassium (E)-4,4'-diphenylstilbene-4"-4"'-disulfonate (stilbene I) [148]
    3.8.2 mms-4-Acetylstilbene [149]
    3.8.3 Methyl 3-(E)- {2-[2-(E)-methoxycarbonylethenyl]cyclopent-1 -enyl(?)acrylate [150]
    3.8.4 Diethyl 4'-chloro-4'-methoxycarbonylspirotcyclopropane-1,3'-bicyclo[4.3.0]non-l'(6')-ene]-8',8'-dicarboxylate [150]
    3.8.5 (?)-2-Cyclohexenyl-2,5-dihydrofuran [151]
    3.8.6 Methoxy-1-GSVethenyl-1,2,3,4- tetrahydronaphthalene [151]
  Acknowledgments [152]
  Abbreviations and acronyms [152]
  References [154]
4 Organotin Reagents in Cross-Coupling Terence N. Mitchell
  4.1 Introduction [167]
  4.2 Stille coupling of alkenyltins [167]
    4.2.1 Inlermolecular reactions [168]
      4.2.1.1 Reactions involving organic halides and inflates [168]
      4.2.1.2 Reactions involving acid chlorides [170]
      4.2.1.3 Reactions involving allyl carbonates [171]
    4.2.2 Intramolecular reactions [172]
    4.2.3 Reactions of distannylalkenes [173]
    4.2.4 Less conventional reactions [175]
    4.2.5 Mechanistic considerations and the choice of catalyst [178]
  4.3 Reactions of substrates where tin is attached to a heterocyclic ring [179]
    4.3.1 Stannylfurans, -thiophenes, and -pyrroles [179]
    4.3.2 Stannylpyridines (and-quinolines) [180]
    4.3.3 Stannylindoles [182]
    4.3.4 Other heterocycles [182]
  4.4 Reactions of aryItins [182]
    4.4.1 Reactions with inflates [182]
    4.4.2 Reactions with halides [183]
  4.5 Reactions of alkynyItins [185]
  4.6 Reactions of alkyltins [187]
  4.7 Reactions involving various types of tetraorganolin [187]
  4.8 Reactions of allyl-, allenyl-, and propargyItins [188]
  4.9 Related palladium-catalyzed reactions [189]
    4.9.1 Reactions of ditins (and silylstannanes) [189]
      4.9.1.1 Cross-coupling reactions [190]
      4.9.1.2 Addition reactions [190]
    4.9.2 Reactions of tin hydrides [190]
    4.9.3 Reactions of tin alkoxides, thioalkoxides, and stannylamines [192]
  4.10 Reactions induced by copper [192]
  4.11 Nickel-catalyzed reactions [193]
  4.12 Mechanistic discussion and conclusion [194]
  4.13 Experimental procedures [195]
    4.13.1 Indanomycin [195]
    4.13.2 N,N'-Bis(trifluoromethanesulfonyl)papuamine [196]
    4.13.3 Rapamycin [196]
    4.13.4 A nickel-catalyzed procedure: 1-Phenylpent-4-en-1-yne [196]
  Abbreviations [197]
  References [197]
5 Cross-coupling Reactions to sp Carbon Atoms Kenkichi Sonogashira
  5.1 Introduction [203]
  5.2 Cross-coupling reactions of alkynylmetal reagents with sp2 carbon atoms [203]
    5.2.1 Alkynylcopper reagents [203]
    5.2.2 Alkynylborane reagents [205]
  5.3 Transition-metal-catalyzed Cross-coupling [206]
    5.3.1 Alkynylzinc reagents [206]
    5.3.2 Alkynyltin reagents [208]
    5.3.3 Alkynylmagnesium reagents [211]
    5.3.4 Alkynylborane reagents [212]
    5.3.5 Terminal acetylene with sp2-carbon halides [213]
      5.3.5.1 Synthesis of internal acetylenes [213]
      5.3.5.2 Synthesis of terminal acetylenes [216]
      5.3.5.3 Stereospecific synthesis [220]
      5.3.5.6 Cross-coupling of haloalkynes with organometallic compounds [222]
  5.4 Conclusions [223]
  5.5 Experimental procedures [224]
    5.5.1 Undeca-3,5-diyn-1-ol [224]
    5.5.2 Alk-3,5-diyn-1-ol [224]
    5.5.3 (E)-5-Undecen-3-yn-1-ol [224]
    5.5.4 Diphenylacetylene [225]
      5.5.5 4-Phenylbut-1-en-3-yne [225]
    5.5.6 (?)-Nitroethynylbenzene [226]
    5.5.7 (7Z)-7-Pentadecen-5,9-yn-1-ol [226]
    5.5.8 Terminal acetylene by potassium-hydroxide-catalyzed retro-Favorsky reaction [226]
  Abbreviations [227]
  References [227]
6 Intramolecular Heck Reactions in Natural Product Chemistry J. T. Link, Larry E. Overman
  6.1 Introduction [231]
  6.2 Mechanistic outline [231]
  6.3 Ring synthesis [233]
    6.3.1 Five-membered rings [233]
    6.3.2 Six-membered rings [236]
    6.3.3 Seven-membered rings [242]
    6.3.4 Eight-membered rings [243]
    6.3.5 Large rings [244]
  6.4 Cycloisomerization of enynes [246]
  6.5 Tandem reactions [248]
  6.6 Asymmetric reactions [256]
  6.7 Concluding comments [260]
  6.8 Representative experimental procedures [261]
    6.8.1 General comments about catalysts, reagents, and conditions [261]
    6.8.2 [7a,8c]-Dispiro[l ,3-dioxolane-2,1 '-cyclohex-2'-ene-4',8"-7"[(methoxycarbonyl)aminomethyl][5H-1,3]dioxor4,5-g][2]benzopyran] [263]
    6.8.3 (-)-5,6-Dehydro-17-[10,11-dihydro-5H-dibenzo[a,J]cyclohepten-5-yl]-4-benzyloxy-3-methoxymorphinan [263]
    6.8.4 (5/3,17/3)-((?)-Methoxybenzyl)oxymethyl-5,19-methylenedioxyandrostan-l,8(14),9(11)-triene [263]
    6.8.5 (2(?),4a5(?),75(?),9a5(?))-2-Hydroxy-4-(4-hydroxybutyl)-7-methyl-1,2,5,6,7, 9a-hexahydro-4a,7-methano-4(?)-benzocycloheptene [264]
    6.8.6 (?)-3-Formylmethyl-1,2-dihydro-5-methoxy-1,3-dimethyl-2-oxo-[3(?)]indole [265]
  Abbreviations [266]
  References [266]
7 Carbometallation Reactions Ilane Marek, Jean F. Normant
  7.1 Introduction [271]
  7.2 Carbometallation of alkynes [271]
    7.2.1 Intermolecular Carbometallation [271]
    7.2.2 Intramolecular Carbometallation [276]
      7.2.2.1 Five-membered ring synthesis [276]
      7.2.2.2 Four-membered ring synthesis [282]
      7.2.2.3 Six-membered ring synthesis [282]
  7.3 Carbometallation of allenes [283]
    7.3.1 Intramolecular Carbometallation [283]
    7.3.2 Intermolecular Carbometallation [286]
  7.4 Carbometallation of conjugated enynes [287]
    7.4.1 Intermolecular Carbometallation [287]
    7.4.2 Intramolecular carbolithiation of conjugated silylated enynes [287]
  7.5 Carbometallation of alkenes [289]
    7.5.1 Intramolecular Carbometallation [290]
      7.5.1.1 Five-membered ring synthesis [290]
      7.5.1.2 Six-membered ring synthesis [304]
      7.5.1.3 Four-membered ring synthesis and rearrangements of bis(homoallyl) metals [305]
      7.5.1.4 Three-membered ring synthesis [306]
      7.5.1.5 Five-membered ring synthesis via cyclization of vinyllithium derivatives [306]
    7.5.2 Inteimolecular Carbometallation [307]
  7.6 Enantioselective Carbometallation of alkenes [322]
  7.7 Conclusions [328]
  7.8 Experimental procedures [329]
    7.8.1 (E)-1-Chloro-2-allyl-3-tert-butoxy)hex-1-ene [329]
    7.8.2 General procedure for the cyclization involving Rieke's activated zinc [330]
    7.8.3 Typical procedure for the cyclization of propargylic organozinc reagents [330]
    7.8.4 anr(?)-(35(?),4(?))-Dimethylnon-1-ene [331]
    7.8.5 ((?))-2-Benzylhexan-1-ol [331]
  Abbreviations [331]
  References and notes [332]
8 Palladium-catalyzed 1,4-Additions to Conjugated Dienes Jan-E. Backvall
  8.1 Introduction [339]
  8.2 Palladium(0)-catalyzed reactions [339]
    8.2.1 Addition of H-Nu [340]
      8.2.1.1 1,4-Hydrosilylation [340]
    8.2.1.2 1,4-Hydrostannation [342]
      8.2.1.3 1,4-Hydroamination [342]
      8.2.1.4 Addition of active methylene compounds [343]
      8.2.1.5 1,4-Hydrosulfonation [344]
      8.2.1.6 1,4-Hydroboration [344]
      8.2.1.7 1,4-Hydrocyanation [345]
    8.2.2 1,4-Coupling with R-and Nu [345]
      8.2.2.1 1,4-Carboamination [346]
      8.2.2.2 1,4-Addition of R-(aryl or vinyl) and stabilized carbanions [347]
      8.2.2.3 1,4-Addition of carbon and oxygen nucleophiles [349]
      8.2.2.4 1,4-Carbosilylation [350]
  8.3 Palladium(II)-catalyzed reactions [352]
    8.3.1 1,4-Addition of two nucleophiles [352]
      8.3.1.1 1,4-Diacyloxylation [353]
      8.3.1.2 1,4-Haloacyloxylation [364]
      8.3.1.3 1,4-Addition of an alkoxide and another oxygen function or a halide [372]
      8.3.1.4 1,4-Oxyanimation and 1,4-chloroamination [376]
      8.3.1.5 Intramolecular 1,4-additions with С—С bond formation [377]
  8.4 Experimental Procedures [380]
    8.4.1 (3aS*,5R*,7aR*)-5-Acetoxy-2-oxo-2,3,3a,4,5,7a-hexahydK)benzofuran [380]
    8.4.2 cis-4-Chloro-3-[4-(benzyloxy)butyl]-2-cyclohexen-1-yl acetate [380]
    8.4.3 (3aR*,5S*,7aR*)-1 -(Benzyloxycarbonyl)-5-chloro-2,3,3a,4,5,7a-hexahydroindole [381]
    8.4.4 (15*,45*,dR*)-4-Chloro-7,7-di(raethoxycarbonyl)-9-methylenebicyclo[4.4.0Jdec-2-ene [381]
  Abbreviations [381]
  References and notes [382]
9 Carbon-Carbon Bond Formation Reactions Mediated by Organozinc Reagents Paul Knochel
  9.1 Introduction [387]
    9.1.1 Methods of preparation of zinc organometallics [388]
  9.2 Uncatalyzed cross-coupling reactions [391]
  9.3 Copper-catalyzed cross-coupling reactions [393]
    9.3.1 Cross-coupling reactions with allylic halides and related reactive halides [393]
    9.3.2 Cross-coupling reactions with alkynyl, alkenyl, and aryl halides [396]
    9.3.3 Cross-coupling reactions with alkyl halides [398]
    9.3.4 Acylation reactions [398]
  9.4 Transition-metal-catalyzed cross-coupling reactions [399]
    9.4.1 Palladium and nickel-catalyzed C —bond formation reactions [399]
      9.4.1.1 Addition to unaclivated double bonds [399]
      9.4.1.2 Addition to unactivated triple bonds: nickel-catalyzed carbozincation [403]
      9.4.1.3 Catalytic Csp3-Csp3 cross-coupling reactions [403]
      9.4.1.4 Palladium-catalyzed cross-coupling between polyfunctional unsaturated substrates [406]
    9.4.2 Cobalt-, manganese-, and iron-catalyzed cross-coupling reactions [407]
      9.4.2.1 Carbonylations and acylations [407]
      9.4.2.2 Cobalt-catalyzed cross-coupling reactions [408]
      9.4.2.3 Manganese- and copper-catalyzed radical cyclizations [409]
  9.5 Conclusions [410]
  9.6 Experimental procedures [410]
    9.6.1 ((?))-6-Chloro-2-hexenenitrile [410]
    9.6.2 (3-Myrtanyl)cyclopentanone [410]
    9.6.3 Quinidine derivative 21 [411]
    9.6.4 6-Chloro-1-cyclohexenyl-1-hexyne [411]
    9.6.5 3-(4-Pentynyl)-2-cyclohexen-1-one [412]
    9.6.6 ((?))-10-Pivaloxy-5-decenemtrile [412]
    9.6.7 10-Nitro-9-phenyldecyl acetate [412]
    9.6.8 2,5-Dibenzoylthiophene [413]
    9.6.9 1-Butyl-1-(3-nitro-2-phenylpropyl)cyclopentane [413]
    9.6.10 Ethyl 12-acetoxy-2-dodecanoate [414]
    9.6.11 ((?))-4-(5-Chloro-1-pentenyl)benzonitrile [414]
    9.6.12 4-Chlorobiphenyl [414]
    9.6.13 (4'-Chloro-3-trifluoromethanesulfonyloxy)biphenyl [414]
    9.6.14 4"-Cyano-4-methoxy-1,1',2',1"-teiphenyl [415]
    9.6.15 Di(4-chlorobutyl) ketone [415]
    9.6.16 5-Oxododecyl Pivalate [416]
    9.6.17 m-Bicyclo[4.3.0]nonan-1-ol [416]
  Abbreviations [416]
  References [416]
10 Organosilicon Compounds in Cross-coupling Reactions Tamejiro Hiyama
  10.1 Introduction [421]
    10.1.1 A brief history of the cross-coupling reaction [421]
    10.1.2 Previous studies on organosilicon-based cross-coupling reactions [421]
    10.1.3 Activation of а С—Si bond by a nucleophile [422]
  10.2 Coupling reactions of alkenylsilanes [423]
    10.2.1 Trimethyl(vinyl)silane [423]
    10.2.2 Alkenylsilanes [424]
    10.2.3 Stereochemistry [425]
    10.2.4 Mechanism [426]
    10.2.5 Synthetic applications [428]
  10.3 Coupling reactions of arylsilanes [429]
    10.3.1 Prototype of biaryl synthesis [429]
    10.3.2 Coupling with chlorobenzene [432]
    10.3.3 Use of sodium hydroxide activator [432]
    10.3.4 Applications [432]
    10.3.5 Carbonylative coupling [433]
    10.3.6 Mechanism [434]
  10.4 Coupling reactions of alkynylsilanes [435]
    10.4.1 Synthesis of conjugated acetylenes [435]
    10.4.2 Three-component coupling reaction [436]
  10.5 Coupling reactions of disilanes [436]
  10.6 Coupling reactions of alkylsilanes [436]
    10.6.1 Methylation [436]
    10.6.2 Alkylation [437]
    10.6.3 Leaving groups of the coupling partner [437]
    10.6.4 Stereochemistry [439]
  10.7 Coupling reactions of allylsilanes [440]
    10.7.1 Regiochemistry [440]
    10.7.2 Stereochemistry [442]
    10.7.3 Asymmetric chemistry [444]
  10.8 Coupling reactions without fluoride ion [446]
    10.8.1 Coupling reactions of allylic carbonates [446]
    10.8.2 Coupling reactions of diene monoxides [448]
  10.9 Prospects [448]
    10.9.1 Availability of organosilicon reagents [448]
    10.9.2 The future of the organosilicon-based cross-coupling reaction [449]
    10.9.3 Summary [449]
  10.10 Experimental procedures [449]
    10.10.1 1-Vinylnaphthalene [449]
    10.10.2 ter(?)-Butyl(3(?),55,6(?))-7-[2-Cyclopropyl-4(4-fluorophenyl)quinolin-3-yl]-3,5-isopropylidenedioxy-6-heptenoate [450]
    10.10.3 4-Fluoro-4'-methoxy-1,1'-biphenyl [450]
    10.10.4 3,4-Difluoro-4'-(fraav-4-propylcyclohexyl)-1,1'-biphenyl [451]
  Abbreviations [451]
  References [452]
11 Palladium-catalyzed Coupling Reactions of Propargylic Compounds Jiro Tsuji, Tadakatsu Mandai
  11.1 Introduction [455]
  11.2 Classification of palladium-catalyzed reactions based on mechanistic considerations [455]
  11.3 Reactions via insertion into the sp2 carbon bond of allenylpalladium intermediates (Type I) [459]
    11.3.1 Reactions of alkenes: formation of 1,2,4-alkatrienes [459]
    11.3.2 Carbonylation [459]
      11.3.2.1 Reaction features [459]
      11.3.2.2 Preparation of 2,3-alkadienoates and their derivatives by monocarbonylation [461]
      11.3.2.3 Preparation of triesters by dicarbonylation [463]
      11.3.2.4 Dicarbonylation of propargyl chloride and alcohols [466]
      11.3.2.5 Preparation of (?)-alkenylidene-(?)-lactones [468]
      11.3.2.6 Preparation of (?)-alkenylidene-(?)-lactams [469]
      11.3.2.7 Carbonylation in the presence of active methylene and methyne compounds [469]
      11.3.2.8 Domino Carbonylation and Diels-Alder reaction [470]
      11.3.2.9 Domino Carbonylation and ene reaction [471]
      11.3.2.10 Preparation of cyclopentenonecarboxylates [473]
  11.4 Reactions via transmetallation of allenylpalladium intermediates and related reactions (Type II) [475]
    11.4.1 Reactions of hard carbon nucleophiles [475]
    11.4.2 Reaction of terminal alkynes: formation of 1,2-alkadien-4-ynes [477]
  11.5 Reactions via attack by soft carbon and oxo nucleophiles on the central carbon of allenylpalladium intermediates (Type III) [479]
    11.5.1 Reactions of soft carbon nucleophiles [479]
    11.5.2 Reaction of oxo nucleophiles [484]
  11.6 Experimental procedures [485]
    11.6.1 Reaction of carbonate with alkenes [485]
    11.6.2 Domino Carbonylation and Diels-Alder reaction [486]
    11.6.3 Reaction with alkyne [487]
    11.6.4 Furan formation by the reaction with acetoacetate [487]
  Abbreviations [487]
  Reference [489]
Author Index [491]
Subject Index [495]
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