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Pure Appl. Chem., 1994, Vol. 66, No. 7, pp. 1439-1446

http://dx.doi.org/10.1351/pac199466071439

Site selective hydrogen/metal exchange: Competition and cooperation between superbases and neighboring groups

M. Schlosser, Ferenc Faigl, Livia Franzini, Hervé Geneste, Georges Katsoulos and G.-F. Zhong

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  • Lochmann Lubomír, Janata Miroslav: 50 years of superbases made from organolithium compounds and heavier alkali metal alkoxides. cent.eur.j.chem. 2014, 12, 537. <http://dx.doi.org/10.2478/s11532-014-0528-0>
  • Harrison-Marchand Anne, Mongin Florence: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 1. Structural Data. Chem. Rev. 2013, 113, 7470. <http://dx.doi.org/10.1021/cr300295w>
  • Mongin Florence, Harrison-Marchand Anne: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs. Chem. Rev. 2013, 113, 7563. <http://dx.doi.org/10.1021/cr3002966>
  • Cooper Robert T., Chadwick F. Mark, Ashley Andrew E., O’Hare Dermot: Synthesis and Characterization of Group 4 Permethylpentalene Dichloride Complexes. Organometallics 2013, 32, 2228. <http://dx.doi.org/10.1021/om400103g>
  • SCHLOSSER M., FAIGL F., FRANZINI L., GENESTE H., KATSOULOS G., ZHONG G.-F.: ChemInform Abstract: Site Selective Hydrogen/Metal Exchange: Competition and Cooperation Between Superbases and Neighboring Groups. ChemInform 2010, 25, no. <http://dx.doi.org/10.1002/chin.199441289>
  • Khartabil Hassan K., Gros Philippe C., Fort Yves, Ruiz-López Manuel F.: Metalation of Pyridines with nBuLi−Li−Aminoalkoxide Mixed Aggregates: The Origin of Chemoselectivity. J Am Chem Soc 2010, 132, 2410. <http://dx.doi.org/10.1021/ja910350q>
  • Clegg William, Conway Ben, García-Álvarez Pablo, Kennedy Alan R., Mulvey Robert E., Russo Luca, Sassmannshausen Jörg, Tuttle Tell: Structural Tracking of the Potassium-Mediated Magnesiation of Anisole. Chem. Eur. J. 2009, 15, 10702. <http://dx.doi.org/10.1002/chem.200901897>
  • Gros Philippe C., Fort Yves: Combinations of Alkyllithiums and Lithium Aminoalkoxides for Generation of Functional Pyridine Organometallics and Derivatives. Eur J Org Chem 2009, 2009, 4199. <http://dx.doi.org/10.1002/ejoc.200900324>
  • Deagostino Annamaria, Prandi Cristina, Toppino Antonio, Venturello Paolo: Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes. Tetrahedron 2008, 64, 10344. <http://dx.doi.org/10.1016/j.tet.2008.08.081>
  • Blangetti Marco, Deagostino Annamaria, Prandi Cristina, Zavattaro Chiara, Venturello Paolo: N-Metalated imines by reaction of 1,1-diethoxybut-2-ene with aromatic nitriles, as useful intermediates for the synthesis of substituted pyrimidines and cyclopentenones. Chem Commun 2008, 1689. <http://dx.doi.org/10.1039/b719462e>
  • Deagostino Annamaria, Prandi Cristina, Zavattaro Chiara, Venturello Paolo: N-Functionalization of Azoles through Coupling Reactions with Alkoxydienyl and Alkoxystyryl Boronic Esters. Eur J Org Chem 2007, 2007, 1318. <http://dx.doi.org/10.1002/ejoc.200600872>
  • Blangetti Marco, Deagostino Annamaria, Rosso Helèna, Prandi Cristina, Zavattaro Chiara, Venturello Paolo: Rapid and Easy Access to (E)-1,3-Enynes, 1,3-Diynes and Allenes Starting from Propargylic Acetals, Exploiting the Different Reactivity of Lithium and Mixed Lithium–Potassium Organometallic Reagents. Eur J Org Chem 2007, 2007, 5867. <http://dx.doi.org/10.1002/ejoc.200700520>
  • Schlosser Manfred, Mongin Florence: Pyridine elaboration through organometallic intermediates: regiochemical control and completeness. Chem Soc Rev 2007, 36, 1161. <http://dx.doi.org/10.1039/b706241a>
  • Schlosser Manfred: CF3-substituierte aromatische und heterocyclische Bausteine. Angew Chem 2006, 118, 5558. <http://dx.doi.org/10.1002/ange.200600449>
  • Schlosser Manfred: CF3-Bearing Aromatic and Heterocyclic Building Blocks. Angew Chem Int Ed 2006, 45, 5432. <http://dx.doi.org/10.1002/anie.200600449>
  • Tilly David, Samanta Subhendu S., Castanet Anne-Sophie, De Asish, Mortier Jacques: The Expedient and Regioselective Metalation of Unprotected Biphenyl-2-, -3-, and -4-carboxylic Acids. Eur J Org Chem 2006, 2006, 174. <http://dx.doi.org/10.1002/ejoc.200500469>
  • Deagostino Annamaria, Prandi Cristina, Zavattaro Chiara, Venturello Paolo: Functionalized 1-Alkoxy-1,3-dienes: Their Preparation and Applications in Synthetic Organic Chemistry. Eur J Org Chem 2006, 2006, 2463. <http://dx.doi.org/10.1002/ejoc.200500944>
  • Deagostino Annamaria, Farina Vittorio, Prandi Cristina, Zavattaro Chiara, Venturello Paolo: New Metal-Catalyzed Synthesis of Quinoline and Chromene Skeletons. Eur J Org Chem 2006, 2006, 3451. <http://dx.doi.org/10.1002/ejoc.200600230>
  • Marzi Elena, Bobbio Carla, Cottet Fabrice, Schlosser Manfred: Converting Core Compounds into Building Blocks: The Concept of Regiochemically Exhaustive Functionalization. Eur J Org Chem 2005, 2005, 2116. <http://dx.doi.org/10.1002/ejoc.200400895>
  • Deagostino Annamaria, Migliardi Manuele, Occhiato Ernesto G., Prandi Cristina, Zavattaro Chiara, Venturello Paolo: LIC-KOR promoted formation of conjugated dienes as useful building blocks for palladium-catalyzed syntheses. Tetrahedron 2005, 61, 3429. <http://dx.doi.org/10.1016/j.tet.2005.01.044>
  • Prandi Cristina, Deagostino Annamaria, Venturello Paolo, Occhiato Ernesto G.: Stereoselective Synthesis of Spirocyclic Ketones by Nazarov Reaction. Org Lett 2005, 7, 4345. <http://dx.doi.org/10.1021/ol051464a>
  • García Graciela V., Nudelman Norma Sbarbati: TANDEM REACTIONS INVOLVING ORGANOLITHIUM REAGENTS. A REVIEW. Org Prep Proced Int 2003, 35, 445. <http://dx.doi.org/10.1080/00304940309355860>
  • Tivola Paolo Balma, Deagostino Annamaria, Prandi Cristina, Venturello Paolo: LIC-KOR-PROMOTED ACCESS TO A TETRAHYDROINDANONE PRECURSOR. Synth Common 2001, 31, 953. <http://dx.doi.org/10.1081/SCC-100103333>
  • Schlosser Manfred, Kotthaus Martina: Isopulegol as a Model Compound: Metalation and Substitution of an Allylic Position in the Presence of an Unprotected Hydroxy Function. Eur J Org Chem 1999, 1999, 459. <http://dx.doi.org/10.1002/(SICI)1099-0690(199902)1999:2<459::AID-EJOC459>3.0.CO;2-F>
  • Tivola Paolo Balma, Deagostino Annamaria, Fenoglio Claudia, Mella Mariella, Prandi Cristina, Venturello Paolo: Mixed Superbase LICKOR as a Key Reagent for the Synthesis of Conjugate Dienes from Citral and Farnesal – A New Route to a Potential Mimic Agent of Juvenile Hormones by Diels–Alder Cycloaddition. Eur J Org Chem 1999, 1999, 2143. <http://dx.doi.org/10.1002/(SICI)1099-0690(199909)1999:9<2143::AID-EJOC2143>3.0.CO;2-C>
  • Wang Qian, Wei Heng-xu, Schlosser Manfred: The Simultaneous In-Situ Generation of Aldehydes and Phosphorus Ylides: A Convenient Multi-Step One-Pot Olefination Protocol. Eur J Org Chem 1999, 1999, 3263. <http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3263::AID-EJOC3263>3.0.CO;2-U>
  • Cominetti Fulvio, Deagostino Annamaria, Prandi Cristina, Venturello Paolo: Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant. Tetrahedron 1998, 54, 14603. <http://dx.doi.org/10.1016/S0040-4020(98)00918-1>
  • Schlosser Manfred, Maccaroni Paola, Marzi Elena: The effect of an alkoxy group on the kinetic and thermodynamic acidity of benzene and toluene. Tetrahedron 1998, 54, 2763. <http://dx.doi.org/10.1016/S0040-4020(98)83011-1>
  • Franzini Livia, Moret Etienne, Schlosser Manfred: Conformational Mobility and Preferences of Allyl-Type Organometallic Intermediates: Dodec-2-enylpotassium. Chem Ber 1997, 130, 83. <http://dx.doi.org/10.1002/cber.19971300113>
  • Moret Etienne, Franzini Livia, Schlosser Manfred: Hydroxy- and Carboxy-Substituted Allylsilanes: A Simple and Stereoselective Method of Preparation. Chem Ber 1997, 130, 335. <http://dx.doi.org/10.1002/cber.19971300306>
  • Deagostino Annamaria, Prandi Cristina, Venturello Paolo: Reaction of α,β-unsaturated and α-phenyl acetals with epoxides, promoted by lithium. Potassium mixed base LICKOR: Synthesis of homoallyl alcohols. Tetrahedron 1996, 52, 1433. <http://dx.doi.org/10.1016/0040-4020(95)00969-8>