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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1063-1069

http://dx.doi.org/10.1351/pac200880051063

Golden opportunities in catalysis

Norbert Krause, Volker Belting, Carl Deutsch, Jörg Erdsack, Hong-Tao Fan, Birgit Gockel, Anja Hoffmann-Röder, Nobuyoshi Morita and Frank Volz

Organic Chemistry II, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany

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  • Obradors Carla, Echavarren Antonio M.: Intriguing mechanistic labyrinths in gold(i) catalysis. Chem. Commun. 2014, 50, 16. <http://dx.doi.org/10.1039/c3cc45518a>
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  • Wan Baoqiang, Ma Shengming: Enantioselective Decarboxylative Amination: Synthesis of Axially Chiral Allenyl Amines. Angew. Chem. Int. Ed. 2013, 52, 441. <http://dx.doi.org/10.1002/anie.201204796>
  • Ye Juntao, Fan Wu, Ma Shengming: tert -Butyldimethylsilyl-Directed Highly Enantioselective Approach to Axially Chiral α-Allenols. Chem. Eur. J. 2013, 19, 716. <http://dx.doi.org/10.1002/chem.201201948>
  • Spina Rosella, Colacino Evelina, Martinez Jean, Lamaty Frédéric: Poly(ethylene glycol) as a Reaction Matrix in Platinum- or Gold-Catalyzed Cycloisomerization: A Mechanistic Investigation. Chem. Eur. J. 2013, 19, 3817. <http://dx.doi.org/10.1002/chem.201203800>
  • Barreiro Elena M., Adrio Luis A., Mimi Hii King Kuok, Brazier John B.: Coinage Metal Catalysts for the Addition of O-H to C=C Bonds. Eur. J. Org. Chem. 2013, 2013, 1027. <http://dx.doi.org/10.1002/ejoc.201201441>
  • Tomás-Mendivil Eder, Toullec Patrick Y., Borge Javier, Conejero Salvador, Michelet Véronique, Cadierno Victorio: Water-Soluble Gold(I) and Gold(III) Complexes with Sulfonated N-Heterocyclic Carbene Ligands: Synthesis, Characterization, and Application in the Catalytic Cycloisomerization of γ-Alkynoic Acids into Enol-Lactones. ACS Catal. 2013, 3, 3086. <http://dx.doi.org/10.1021/cs4009144>
  • Jiang Guo-Jie, Zheng Qin-Heng, Dou Meng, Zhuo Lian-Gang, Meng Wei, Yu Zhi-Xiang: Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ). J. Org. Chem. 2013, 78, 11783. <http://dx.doi.org/10.1021/jo4018183>
  • Manzuna Sapu Chicco, Deska Jan: Chemoenzymatic total synthesis of hyperiones A and B. Org. Biomol. Chem. 2013, 11, 1376. <http://dx.doi.org/10.1039/c2ob27073k>
  • López-Gómez María J., Martin David, Bertrand Guy: Anti-Bredt N-heterocyclic carbene: an efficient ligand for the gold(i)-catalyzed hydroamination of terminal alkynes with parent hydrazine. Chem. Commun. 2013, 49, 4483. <http://dx.doi.org/10.1039/c3cc41279b>
  • Yu Shichao, Ma  Shengming: Allene in katalytischer asymmetrischer Synthese und Naturstoffsynthese. angew chemie 2012, 124, 3128. <http://dx.doi.org/10.1002/ange.201101460>
  • Yu Shichao, Ma Shengming: Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses. Angew Chem Int E 2012, 51, 3074. <http://dx.doi.org/10.1002/anie.201101460>
  • Boutier Audrey, Kammerer-Pentier Claire, Krause Norbert, Prestat Guillaume, Poli Giovanni: Pd-Catalyzed Asymmetric Synthesis of N-Allenyl Amides and Their Au-Catalyzed Cycloisomerizative Hydroalkylation: A New Route Toward Enantioenriched Pyrrolidones. Chemistry A European Journal 2012, 18, 3840. <http://dx.doi.org/10.1002/chem.201103902>
  • Hashmi A. Stephen K., Ghanbari Mohammad, Rudolph Matthias, Rominger Frank: Combining Gold and Palladium Catalysis: One-Pot Access to Pentasubstituted Arenes from Furan-Yne and En-Diyne Substrates. Chem. Eur. J. 2012, 18, 8113. <http://dx.doi.org/10.1002/chem.201200091>
  • Krause Norbert, Aksin-Artok Özge, Asikainen Martta, Breker Viola, Deutsch Carl, Erdsack Jörg, Fan Hong-Tao, Gockel Birgit, Minkler Stefan, Poonoth Manojkumar: Combined coinage metal catalysis for the synthesis of bioactive molecules. J Organomet Chem 2012, 704, 1. <http://dx.doi.org/10.1016/j.jorganchem.2012.01.008>
  • Benetti Simonetta, De Risi Carmela, Pollini Gian P., Zanirato Vinicio: Synthetic Routes to Chiral Nonracemic and Racemic Dihydro- And Tetrahydrothiophenes. Chemistry Review 2012, 112, 2129. <http://dx.doi.org/10.1021/cr200298b>
  • Ye Juntao, Li Suhua, Chen Bo, Fan Wu, Kuang Jinqiang, Liu Jinxian, Liu Yu, Miao Bukeyan, Wan Baoqiang, Wang Yuli: Catalytic Asymmetric Synthesis of Optically Active Allenes from Terminal Alkynes. Org Lett 2012, 120222112158003. <http://dx.doi.org/10.1021/ol300296k>
  • Sun Tao, Deutsch Carl, Krause Norbert: Combined coinage metal catalysis in natural product synthesis: total synthesis of (+)-varitriol and seven analogs. Org. Biomol. Chem. 2012, 10, 5965. <http://dx.doi.org/10.1039/c2ob25069a>
  • Aksın-Artok Özge, Krause Norbert: Combined Rhodium/Gold Catalysis: From Propargyloxiranes to 2,5-Dihydrofurans in One Pot. Synth Catal 2011, 353, 385. <http://dx.doi.org/10.1002/adsc.201000903>
  • Xiao Ya-Ping, Liu Xin-Yuan, Che Chi-Ming: Efficient Gold(I)-Catalyzed Direct Intramolecular Hydroalkylation of Unactivated Alkenes with α-Ketones. Angew Chem 2011, 123, 5039. <http://dx.doi.org/10.1002/ange.201100044>
  • Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine. angew chemie 2011, 123, 5674. <http://dx.doi.org/10.1002/ange.201100740>
  • Minkler Stefan R. K., Lipshutz Bruce H., Krause Norbert: Gold Catalysis in Micellar Systems. angew chemie 2011, 123, 7966. <http://dx.doi.org/10.1002/ange.201101396>
  • Xiao Ya-Ping, Liu Xin-Yuan, Che Chi-Ming: Efficient Gold(I)-Catalyzed Direct Intramolecular Hydroalkylation of Unactivated Alkenes with α-Ketones. Angew Chem Int Ed 2011, 50, 4937. <http://dx.doi.org/10.1002/anie.201100044>
  • Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine. Angew. Chem. Int. Ed. 2011, 50, 5560. <http://dx.doi.org/10.1002/anie.201100740>
  • Minkler Stefan R. K., Lipshutz Bruce H., Krause Norbert: Gold Catalysis in Micellar Systems. Angew Chem Int E 2011, 50, 7820. <http://dx.doi.org/10.1002/anie.201101396>
  • Liu Xin-Yuan, Guo Zhen, Dong Sijia S., Li Xiao-Hua, Che Chi-Ming: Highly Efficient and Diastereoselective Gold(I)-Catalyzed Synthesis of Tertiary Amines from Secondary Amines and Alkynes: Substrate Scope and Mechanistic Insights. Chemistry A European Journal 2011, 17, 12932. <http://dx.doi.org/10.1002/chem.201101982>
  • Montaignac Benjamin, Vitale Maxime R., Ratovelomanana-Vidal Virginie, Michelet Véronique: Cooperative Copper(I) and Primary Amine Catalyzed Room-Temperature Carbocyclization of Formyl Alkynes. Eur J Org Chem 2011, 2011, 3723. <http://dx.doi.org/10.1002/ejoc.201100464>
  • Gouault Nicolas, Le Roch Myriam, Cheignon Adèle, Uriac Philippe, David Michèle: Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines. Org Lett 2011, 13, 4371. <http://dx.doi.org/10.1021/ol201698m>
  • Fernández-García Jesús Manuel, Fernández-Rodríguez Manuel Á., Aguilar Enrique: Catalytic Intermolecular Hetero-Dehydro-Diels–Alder Cycloadditions: Regio- and Diasteroselective Synthesis of 5,6-Dihydropyridin-2-ones. Org Lett 2011, 13, 5172. <http://dx.doi.org/10.1021/ol202046y>
  • Martin David, Melaimi Mohand, Soleilhavoup Michele, Bertrand Guy: A Brief Survey of Our Contribution to Stable Carbene Chemistry. Organomettalics 2011, 30, 5304. <http://dx.doi.org/10.1021/om200650x>
  • Rudolph Matthias, Hashmi A. Stephen K.: Heterocycles from gold catalysis. Chem Commun 2011, 47, 6536. <http://dx.doi.org/10.1039/c1cc10780a>
  • Zeng Xiaoming, Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Serendipitous Discovery of the Catalytic Hydroammoniumation and Methylamination of Alkynes. Angew Chem 2010, 122, 954. <http://dx.doi.org/10.1002/ange.200905341>
  • Melaimi Mohand, Soleilhavoup Michèle, Bertrand Guy: Stabile cyclische Carbene und verwandte Spezies jenseits der Diaminocarbene. Angew Chem 2010, 122, 8992. <http://dx.doi.org/10.1002/ange.201000165>
  • Zeng Xiaoming, Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Serendipitous Discovery of the Catalytic Hydroammoniumation and Methylamination of Alkynes. Angew Chem Int E 2010, 49, 942. <http://dx.doi.org/10.1002/anie.200905341>
  • Melaimi Mohand, Soleilhavoup Michèle, Bertrand Guy: Stable Cyclic Carbenes and Related Species beyond Diaminocarbenes. Angew Chem Int Ed 2010, 49, 8810. <http://dx.doi.org/10.1002/anie.201000165>
  • Saget Tanguy, Cramer Nicolai: Heteroatom-Nucleophile-Induced CC Fragmentations: Synthesis of Allenes and Entry to Domino Reactions. Angew Chem Int Ed 2010, 49, 8962. <http://dx.doi.org/10.1002/anie.201004795>
  • Gockel Birgit, Krause Norbert: Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold-Catalyzed Cyclization/Cross Coupling Sequence. Eur J Org Chem 2010, 2010, 311. <http://dx.doi.org/10.1002/ejoc.200901010>
  • Demir Ayhan S., Emrullahoğlu Mustafa, Buran Kerem: Gold(i)/Zn(ii) catalyzed tandem hydroamination/annulation reaction of 4-yne-nitriles. Chem Commun 2010, 46, 8032. <http://dx.doi.org/10.1039/c0cc02357d>
  • Krause Norbert, Aksin-Artok Özge, Breker Viola, Deutsch Carl, Gockel Birgit, Poonoth Manojkumar, Sawama Yoshinari, Sawama Yuka, Sun Tao, Winter Christian: Combined coinage metal catalysis for the synthesis of bioactive molecules. Pure and App Chemis 2010, 1. <http://dx.doi.org/10.1351/PAC-CON-09-09-23>
  • Poonoth Manojkumar, Krause Norbert: Stereoselective Synthesis of Conjugated Bisallenols as Precursors of Novel Bis(2,5-dihydrofuran) Derivatives. Adv Synth Catal 2009, 351, 117. <http://dx.doi.org/10.1002/adsc.200800469>
  • Asikainen Martta, Krause Norbert: Tandem Enzyme/Gold-Catalysis: From Racemic α-Allenic Acetates to Enantiomerically Enriched 2,5-Dihydrofurans in One Pot. Adv Synth Catal 2009, 351, 2305. <http://dx.doi.org/10.1002/adsc.200900434>
  • Kim Soo Min, Park Ji Hoon, Kang Youn Kyung, Chung Young Keun: N-Heterocyclic Carbene Gold(I) Catalyzed Transformation of N-Tethered 1,5-Bisallenes to 6,7-Dimethylene-3-azabicyclo[3.1.1]heptanes. Angew Chem 2009, 121, 4602. <http://dx.doi.org/10.1002/ange.200806394>
  • Winter Christian, Krause Norbert: Strukturelle Vielfalt durch Goldkatalyse: stereoselektive Synthese von N-Hydroxypyrrolinen, Dihydroisoxazolen und Dihydro-1,2-oxazinen. Angew Chem 2009, 121, 6457. <http://dx.doi.org/10.1002/ange.200902355>
  • Kim Soo Min, Park Ji Hoon, Kang Youn Kyung, Chung Young Keun: N-Heterocyclic Carbene Gold(I) Catalyzed Transformation of N-Tethered 1,5-Bisallenes to 6,7-Dimethylene-3-azabicyclo[3.1.1]heptanes. Angew Chem Int Ed 2009, 48, 4532. <http://dx.doi.org/10.1002/anie.200806394>
  • Winter Christian, Krause Norbert: Structural Diversity through Gold Catalysis: Stereoselective Synthesis of N-Hydroxypyrrolines, Dihydroisoxazoles, and Dihydro-1,2-oxazines. Angew Chem Int Ed 2009, 48, 6339. <http://dx.doi.org/10.1002/anie.200902355>
  • Zeng Xiaoming, Frey Guido D., Kousar Shazia, Bertrand Guy: A Cationic Gold(I) Complex as a General Catalyst for the Intermolecular Hydroamination of Alkynes: Application to the One-Pot Synthesis of Allenes from Two Alkynes and a Sacrificial Amine. Chem Eur J 2009, 15, 3056. <http://dx.doi.org/10.1002/chem.200802626>
  • Arcadi Antonio, Alfonsi Maria, Chiarini Marco, Marinelli Fabio: Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds. J Organomet Chem 2009, 694, 576. <http://dx.doi.org/10.1016/j.jorganchem.2008.12.013>
  • Volz Frank, Wadman Sipke H., Hoffmann-Röder Anja, Krause Norbert: Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine. Tetrahedron 2009, 65, 1902. <http://dx.doi.org/10.1016/j.tet.2008.11.104>
  • Nishina Naoko, Yamamoto Yoshinori: Gold-catalyzed hydrofunctionalization of allenes with nitrogen and oxygen nucleophiles and its mechanistic insight. Tetrahedron 2009, 65, 1799. <http://dx.doi.org/10.1016/j.tet.2008.11.106>
  • Mauleón Pablo, Krinsky Jamin L., Toste F. Dean: Mechanistic Studies on Au(I)-Catalyzed [3,3]-Sigmatropic Rearrangements using Cyclopropane Probes. J Am Chem Soc 2009, 131, 4513. <http://dx.doi.org/10.1021/ja900456m>
  • Zeng Xiaoming, Frey Guido D., Kinjo Rei, Donnadieu Bruno, Bertrand Guy: Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives. J Am Chem Soc 2009, 131, 8690. <http://dx.doi.org/10.1021/ja902051m>
  • Winter Christian, Krause Norbert: Towards sustainable homogeneous gold catalysis: cycloisomerization of functionalized allenes in water. Green Chem 2009, 11, 1309. <http://dx.doi.org/10.1039/b905823k>
  • Wegner Hermann A., Ahles Sebastian, Neuburger Markus: A New Gold-Catalyzed Domino Cyclization and Oxidative Coupling Reaction. Chem Eur J 2008, 14, 11310. <http://dx.doi.org/10.1002/chem.200801848>
  • Krause Norbert, Belting Volker, Deutsch Carl, Erdsack Joerg, Fan Hong-Tao, Gockel Birgit, Hoffmann-Roeder Anja, Morita Nobuyoshi, Volz Frank: ChemInform Abstract: Golden Opportunities in Catalysis. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200842259>