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Pure Appl. Chem., 1990, Vol. 62, No. 10, pp. 1867-1878

http://dx.doi.org/10.1351/pac199062101867

Synthetic methodology involving the carbopalladation of allenes

Bernard Cazes

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  • Le Bras Jean, Muzart Jacques: Palladium-catalysed inter- and intramolecular formation of C–O bonds from allenes. Chem. Soc. Rev. 2014, 43, 3003. <http://dx.doi.org/10.1039/c3cs60379b>
  • Lechel Tilman, Pfrengle Fabian, Reissig Hans-Ulrich, Zimmer Reinhold: Three Carbons for Complexity! Recent Developments of Palladium-Catalyzed Reactions of Allenes. ChemCatChem 2013, 5, 2100. <http://dx.doi.org/10.1002/cctc.201200875>
  • Canovese Luciano, Visentin Fabiano, Levi Carlo, Santo Claudio: Synthesis of novel heteroditopic carbene–pyridine palladium(II) chloro vinyl complexes. Comparative reactivity of different palladium vinyl derivatives toward transmetalation with alkynyl stannane. Inorganic Chemistry Communications 2013, 32, 74. <http://dx.doi.org/10.1016/j.inoche.2013.03.026>
  • Xie Xi, Ma Shengming: Palladium-catalyzed asymmetric coupling cyclization of terminal γ-allenols with aryl iodides. Chem. Commun. 2013, 49, 5693. <http://dx.doi.org/10.1039/c3cc40892b>
  • García-López José-Antonio, Saura-Llamas Isabel, McGrady John E., Bautista Delia, Vicente José: Insertion of Allenes into the Pd–C Bond of Ortho-Palladated Primary Arylamines of Biological Relevance: Phenethylamine, Phentermine, (l)-Phenylalanine Methyl Ester, and (l)-Tryptophan Methyl Ester. Synthesis of Tetrahydro-3-benzazepines and Their Salts. Organometallics 2012, 31, 8333. <http://dx.doi.org/10.1021/om300928j>
  • CAZES B.: ChemInform Abstract: Synthetic Methodology Involving the Carbopalladation of Allenes. ChemInform 2010, 22, no. <http://dx.doi.org/10.1002/chin.199107315>
  • Shu Wei, Ma Shengming: Synthesis of a new spiro-BOX ligand and its application in enantioselective allylic cyclization based on carbopalladation of allenyl hydrazines. Chem Commun 2009, 6198. <http://dx.doi.org/10.1039/b912108k>
  • Cheng Chien-Hong, Jeganmohan Masilamani: Transition metal-catalyzed three-component coupling of allenes and the related allylation reactions. Chem Commun 2008, 3101. <http://dx.doi.org/10.1039/b800440d>
  • Tonogaki Keisuke, Itami Kenichiro, Yoshida Jun-ichi: Sequential Pd- and Rh-Catalyzed Three-Component Cyclization with Allenylboronate Platform. Org Lett 2006, 8, 1419. <http://dx.doi.org/10.1021/ol060197l>
  • Grigg Ronald, Hasakunpaisarn Anuch, Kilner Colin, Kongkathip Boonsong, Kongkathip Ngampong, Pettman Alan, Sridharan Visuvanathar: Catalytic processes for the functionalisation and desymmetrisation of malononitrile derivatives. Tetrahedron 2005, 61, 9356. <http://dx.doi.org/10.1016/j.tet.2005.07.048>
  • Fu Chunling, Li Jing, Ma Shengming: Efficient two-step synthesis of 3-halo-3-enals or 2-halo-2-alkenyl ketones from propargylic bromides via a unique cationic 1,2-aryl or proton shift in electrophilic addition reaction of 2,3-allenols with X+. Chem Commun 2005, 4119. <http://dx.doi.org/10.1039/b508069j>
  • Canovese Luciano, Chessa Gavino, Visentin Fabiano, Uguagliati Paolo: Pyridylthioethers: a promising class of polydentate ligands in palladium and platinum coordination. Coord Chem Rev - 2004, 248, 945. <http://dx.doi.org/10.1016/j.ccr.2004.05.009>
  • Ma Shengming, Jiao Ning, Zheng Zilong, Ma Zhichao, Lu Zhan, Ye Longwu, Deng Youqian, Chen Guofei: Cu- and Pd-Catalyzed Asymmetric One-Pot Tandem Addition−Cyclization Reaction of 2-(2‘,3‘-Alkadienyl)-β-keto Esters, Organic Halides, and Dibenzyl Azodicarboxylate:  An Effective Protocol for the Enantioselective Synthesis of Pyrazolidine Derivatives. Org Lett 2004, 6, 2193. <http://dx.doi.org/10.1021/ol0493498>
  • Rasparini Marcello, Sridharan Visuvanathar, Cleghorn Laura A.T, Cooper Ian R, Fishwick Colin W.G, Grigg Ronald, MacLachlan William S: Three-component bimetallic (Pd/In) mediated cascade allylation of C=X functionality. J Organomet Chem 2003, 687, 483. <http://dx.doi.org/10.1016/j.jorganchem.2003.09.047>
  • Rousset Séverine, Abarbri Mohamed, Thibonnet Jérôme, Parrain Jean-Luc, Duchêne Alain: Regio- and stereoselective preparation of γ-alkylidenebutenolides or α-pyrones using a Stille reaction and palladium-catalysed oxacyclisation sequence. Tetrahetron Lett 2003, 44, 7633. <http://dx.doi.org/10.1016/j.tetlet.2003.08.043>
  • Canovese Luciano, Chessa Gavino, Santo Claudio, Visentin Fabiano, Uguagliati Paolo: Insertion of 1,1-Me2propadiene across the Pd–C bond of pyridyl–thioether methyl complexes. A mechanistic study. Inorg Chim Ada 2003, 346, 158. <http://dx.doi.org/10.1016/S0020-1693(02)01432-9>
  • Canovese Luciano, Visentin Fabiano, Chessa Gavino, Santo Claudio, Uguagliati Paolo, Bandoli Giuliano: The marked influence of steric and electronic properties of ancillary pyridylthioether ligands on the rate of allene insertion into the palladium–carbon bond. J Organomet Chem 2002, 650, 43. <http://dx.doi.org/10.1016/S0022-328X(02)01145-2>
  • Oh Chang Ho, Jung Seung Hyun, Bang Su Youn, Park Dai In: Decarbopalladation of π-Allylpalladium Intermediates Formed from Palladium-Catalyzed Arylations of 3-Allen-1-ols. Org Lett 2002, 4, 3325. <http://dx.doi.org/10.1021/ol026659m>
  • Steinig Arno G., de Meijere Armin: Palladium-Catalyzed Bicyclization of 2-Bromo-1,6-dienes and -1,6-enynes to 5-Membered-Ring-Annelated Vinylcyclopropane Derivatives. Eur J Org Chem 1999, 1999, 1333. <http://dx.doi.org/10.1002/(SICI)1099-0690(199906)1999:6<1333::AID-EJOC1333>3.0.CO;2-G>
  • Grigg Ronald, Monteith Michael, Sridharan Visuvanathar, Terrier Catherine: Palladium catalysed reactions of allenes, carbon monoxide and nucleophiles. Tetrahedron 1998, 54, 3885. <http://dx.doi.org/10.1016/S0040-4020(98)00115-X>
  • Gamez Patrick, Ariente Cécile, Goré Jacques, Cazes Bernard: Synthesis of cross-conjugated dienic alcohols. Tetrahedron 1998, 54, 14825. <http://dx.doi.org/10.1016/S0040-4020(98)00944-2>
  • Gamez Patrick, Ariente Cécile, Goré Jacques, Cazes Bernard: Stereoselectivity of the carbopalladation-functionalization of allenic compounds: A mechanistic study. Tetrahedron 1998, 54, 14835. <http://dx.doi.org/10.1016/S0040-4020(98)00945-4>
  • Kang Suk-Ku, Yamaguchi Tokutaro, Pyun Sung-Jae, Lee Yong-Tack, Baik Tae-Gon: Palladium-catalyzed arylation of α-allenic alcohols with hypervalent iodonium salts: Synthesis of epoxides and diol cyclic carbonates. Tetrahetron Lett 1998, 39, 2127. <http://dx.doi.org/10.1016/S0040-4039(98)00076-8>
  • Jonasson Catrin, Bäckvall Jan-E.: Palladium-catalyzed intramolecular 1,2-oxidation of allenes. Tetrahetron Lett 1998, 39, 3601. <http://dx.doi.org/10.1016/S0040-4039(98)00559-0>
  • Owada Yufu, Matsuo Takeshi, Iwasawa Nobuharu: Transformation of 1-(1,2-propadienyl)cyclopropanols into substituted hydroquinones employing octacarbonyldicobalt. Tetrahedron 1997, 53, 11069. <http://dx.doi.org/10.1016/S0040-4020(97)00367-0>
  • Bäckvall Jan-E., Jonasson Catrin: Palldium-catalyzed 1,2-oxidation of allenes. Tetrahetron Lett 1997, 38, 291. <http://dx.doi.org/10.1016/S0040-4039(96)02295-2>
  • Grigg Ronald, Pratt Robert: Palladium catalysed pentamolecular queuing cascades. Tetrahetron Lett 1997, 38, 4489. <http://dx.doi.org/10.1016/S0040-4039(97)00908-8>
  • Grigg Ronald, Brown Stephen, Sridharan Visuvanathar, Uttley Michael D.: Palladium catalysed tetramolecular cascade processes incorporating allene and carbon monoxide. Tetrahetron Lett 1997, 38, 5031. <http://dx.doi.org/10.1016/S0040-4039(97)01062-9>
  • Vicart Nicolas, Cazes Bernard, Gore Jacques: Carbopalladation-sulphonylation of allene: A versatile preparation of 2-vinyl or 2-aryl allyl sulphones. Tetrahedron 1996, 52, 9101. <http://dx.doi.org/10.1016/0040-4020(96)00461-9>
  • Grigg Ronald, Sansano JoséM: Sequential hydrostannylation-cyclisation of δ- and ω-allenyl aryl halides. Cyclisation at the proximal carbon. Tetrahedron 1996, 52, 13441. <http://dx.doi.org/10.1016/0040-4020(96)00801-0>
  • Desarbre Eric, Mérour Jean-Yves: Palladium heteroannulation process for synthesis of substituted pyrrolo[2,3-b]pyridin-3-ones. Tetrahetron Lett 1996, 37, 43. <http://dx.doi.org/10.1016/0040-4039(95)02079-9>
  • Chengebroyen J., Pfeffer M., Sirlin C.: Palladium-assisted intramolecular formation of n-heterocycles by sp2 N nucleophilic attack on η3-allyl-Pd complexes generated by allene insertion into σ PdC bond. Tetrahetron Lett 1996, 37, 7263. <http://dx.doi.org/10.1016/0040-4039(96)01660-7>
  • Xu Yuan-yao, Jin Fu-qiang, Huang Wei-yuan: Facile nucleophilic addition of thiols to 1,1-difluoroallene: a convenient approach to γ,γ-difluoroallyl sulphides. J FLUORINE CHEM 1995, 70, 5. <http://dx.doi.org/10.1016/0022-1139(94)03144-O>
  • Vicart Nicolas, Cazes Bernard, Goré Jacques: Reactivity of 1-alkoxy π-allylpalladium complexes. Tetrahetron Lett 1995, 36, 535. <http://dx.doi.org/10.1016/0040-4039(94)02334-8>
  • Yamamoto Yoshinori, Al-Masum Mohammad, Fujiwara Naoya, Asao Naoki: Remarkable reversal of the regioselectivity in the palladium catalyzed hydrocarbonation reaction of allenes with methylmalononitrile. Tetrahetron Lett 1995, 36, 2811. <http://dx.doi.org/10.1016/0040-4039(95)00403-Y>
  • Besson Laure, Goré Jacques, Cazes Bernard: Palladium-catalyzed addition of malonate type compounds to allenes via a hydropalladation process. Tetrahetron Lett 1995, 36, 3853. <http://dx.doi.org/10.1016/0040-4039(95)00655-V>
  • Walkup Robert D., Guan Lufeng, Kim Young Soo, Kim Sang Woong: A palladium-catalyzed cyclization-carbonylation-coupling reaction between aryl halides and γ-Hydroxyallenes to form aryl (tetrahydrofuran-2-yl)vinyl ketones. Tetrahetron Lett 1995, 36, 3805. <http://dx.doi.org/10.1016/0040-4039(95)00666-Z>
  • Vicart Nicolas, Cazes Bernard, Goré Jacques: Synthesis of α or β-aminodienes via the carbopalladation of 1,2-propadiene. Tetrahetron Lett 1995, 36, 5015. <http://dx.doi.org/10.1016/0040-4039(95)00936-7>
  • Besson L., Bazin J., Gore J., Cazes B.: Palladium-catalysed alkylative cyclisation of 2,3-butadienylmalonates to γ-lactones. Tetrahetron Lett 1994, 35, 2881. <http://dx.doi.org/10.1016/S0040-4039(00)76649-4>
  • Donaldson William A., Bell Peter T., Jin Myung-Jong: Synthesis and reactivity of tricarbonyl(η5-4-triethylsilyl-1methylpentadienyl) iron(+1) cation. J Organomet Chem 1992, 441, 449. <http://dx.doi.org/10.1016/0022-328X(92)80176-X>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1990. J Organomet Chem 1992, 422, 301. <http://dx.doi.org/10.1016/0022-328X(92)88031-D>
  • Chaptal Nathalie, Colovray-Gotteland Véronique, Grandjean Cyrille, Cazes Bernard, Goré Jacques: Carbopalladation of functionalized allenes : regioselectivity of the reaction of carbonucleophiles with the intermediate π-allyl palladium complexes. Tetrahetron Lett 1991, 32, 1795. <http://dx.doi.org/10.1016/S0040-4039(00)74332-2>