CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2012, Vol. 84, No. 8, pp. 1729-1739

http://dx.doi.org/10.1351/PAC-CON-11-10-18

Published online 2012-03-13

Formation of C–C bonds via ruthenium-catalyzed transfer hydrogenation

Joseph Moran and Michael J. Krische*

Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, TX 78712‑1167, USA

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Zhang Yao, Lim Ching-Si, Sim Derek Sui Boon, Pan Hui-Jie, Zhao Yu: Catalytic Enantioselective Amination of Alcohols by the Use of Borrowing Hydrogen Methodology: Cooperative Catalysis by Iridium and a Chiral Phosphoric Acid. Angew. Chem. 2014, 126, 1423. <http://dx.doi.org/10.1002/ange.201307789>
  • McInturff Emma L., Nguyen Khoa D., Krische Michael J.: Redox-Triggered CC Coupling of Diols and Alkynes: Synthesis of β,γ-Unsaturated α-Hydroxyketones and Furans by Ruthenium-Catalyzed Hydrohydroxyalkylation. Angew. Chem. 2014, 126, 3296. <http://dx.doi.org/10.1002/ange.201311130>
  • Zhang Yao, Lim Ching-Si, Sim Derek Sui Boon, Pan Hui-Jie, Zhao Yu: Catalytic Enantioselective Amination of Alcohols by the Use of Borrowing Hydrogen Methodology: Cooperative Catalysis by Iridium and a Chiral Phosphoric Acid. Angew. Chem. Int. Ed. 2014, 53, 1399. <http://dx.doi.org/10.1002/anie.201307789>
  • McInturff Emma L., Nguyen Khoa D., Krische Michael J.: Redox-Triggered CC Coupling of Diols and Alkynes: Synthesis of β,γ-Unsaturated α-Hydroxyketones and Furans by Ruthenium-Catalyzed Hydrohydroxyalkylation. Angew. Chem. Int. Ed. 2014, 53, 3232. <http://dx.doi.org/10.1002/anie.201311130>
  • Pospech Jola, Tlili Anis, Spannenberg Anke, Neumann Helfried, Beller Matthias: Regioselective Ruthenium-Catalyzed Carbonylative Direct Arylation of Five-Membered and Condensed Heterocycles. Chem. Eur. J. 2014, 20, 3135. <http://dx.doi.org/10.1002/chem.201304314>
  • Geary Laina M., Chen Te-Yu, Montgomery T. Patrick, Krische Michael J.: Benzannulation via Ruthenium-Catalyzed Diol–Diene [4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes and Acenes. J. Am. Chem. Soc. 2014, 140411153233006. <http://dx.doi.org/10.1021/ja502659t>
  • Klatt Thomas, Markiewicz John T., Sämann Christoph, Knochel Paul: Strategies To Prepare and Use Functionalized Organometallic Reagents. J. Org. Chem. 2014, 140408080832000. <http://dx.doi.org/10.1021/jo500297r>
  • Shen Jiaxuan, Yang Dejun, Liu Yuxiao, Qin Shuangshuang, Zhang Jingwu, Sun Jiangkai, Liu Chunhui, Liu Chaoyang, Zhao Xiaomei, Chu Changhu, Liu Renhua: Copper-Catalyzed Aerobic Oxidative Coupling of Aromatic Alcohols and Acetonitrile to β-Ketonitriles. Org. Lett. 2014, 16, 350. <http://dx.doi.org/10.1021/ol403555n>
  • Itoh Takahiko, Montgomery T. Patrick, Recio Antonio, Krische Michael J.: Asymmetric Alcohol C–H Allylation and syn-Crotylation: C9–C20 of Tetrafibricin. Org. Lett. 2014, 16, 820. <http://dx.doi.org/10.1021/ol403566w>
  • Dechert-Schmitt Anne-Marie R., Schmitt Daniel C., Gao Xin, Itoh Takahiko, Krische Michael J.: Polyketide construction via hydrohydroxyalkylation and related alcohol C–H functionalizations: reinventing the chemistry of carbonyl addition. Nat. Prod. Rep. 2014, 31, 504. <http://dx.doi.org/10.1039/c3np70076c>
  • Dechert-Schmitt Anne-Marie R., Schmitt Daniel C., Krische Michael J.: Protecting-Group-Free Diastereoselective CC Coupling of 1,3-Glycols and Allyl Acetate through Site-Selective Primary Alcohol Dehydrogenation. Angew. Chem. 2013, 125, 3277. <http://dx.doi.org/10.1002/ange.201209863>
  • Waldeck Andrew R., Krische Michael J.: Total Synthesis of Cyanolide A in the Absence of Protecting Groups, Chiral Auxiliaries, or Premetalated Carbon Nucleophiles. Angew. Chem. 2013, 125, 4566. <http://dx.doi.org/10.1002/ange.201300843>
  • Yamaguchi Eiji, Mowat Jeffrey, Luong Tom, Krische Michael J.: Regio- and Diastereoselective CC Coupling of α-Olefins and Styrenes to 3-Hydroxy-2-oxindoles by Ru-Catalyzed Hydrohydroxyalkylation. Angew. Chem. 2013, 125, 8586. <http://dx.doi.org/10.1002/ange.201303552>
  • Quintard Adrien, Constantieux Thierry, Rodriguez Jean: An Iron/Amine-Catalyzed Cascade Process for the Enantioselective Functionalization of Allylic Alcohols. Angew. Chem. 2013, 125, 13121. <http://dx.doi.org/10.1002/ange.201307295>
  • Dechert-Schmitt Anne-Marie R., Schmitt Daniel C., Krische Michael J.: Protecting-Group-Free Diastereoselective CC Coupling of 1,3-Glycols and Allyl Acetate through Site-Selective Primary Alcohol Dehydrogenation. Angew. Chem. Int. Ed. 2013, 52, 3195. <http://dx.doi.org/10.1002/anie.201209863>
  • Waldeck Andrew R., Krische Michael J.: Total Synthesis of Cyanolide A in the Absence of Protecting Groups, Chiral Auxiliaries, or Premetalated Carbon Nucleophiles. Angew. Chem. Int. Ed. 2013, 52, 4470. <http://dx.doi.org/10.1002/anie.201300843>
  • Yamaguchi Eiji, Mowat Jeffrey, Luong Tom, Krische Michael J.: Regio- and Diastereoselective CC Coupling of α-Olefins and Styrenes to 3-Hydroxy-2-oxindoles by Ru-Catalyzed Hydrohydroxyalkylation. Angew. Chem. Int. Ed. 2013, 52, 8428. <http://dx.doi.org/10.1002/anie.201303552>
  • Quintard Adrien, Constantieux Thierry, Rodriguez Jean: An Iron/Amine-Catalyzed Cascade Process for the Enantioselective Functionalization of Allylic Alcohols. Angew. Chem. Int. Ed. 2013, 52, 12883. <http://dx.doi.org/10.1002/anie.201307295>
  • Weickmann Daniel, Plietker Bernd: The Ru-Catalyzed Alkylative Dearyloxylation of L-type 2-Aryloxyethanols. ChemCatChem 2013, 5, 2170. <http://dx.doi.org/10.1002/cctc.201300177>
  • Lee Jae Seung, Kim Dongeun, Kong Suk Bin, Han Hyunsoo: Air-Stable Bifunctional Allylation Reagents for the Asymmetric Synthesis of Differentiated syn - and anti -1,3-Diols. Chem. Eur. J. 2013, 19, 4135. <http://dx.doi.org/10.1002/chem.201204148>
  • Fleischer Ivana, Wu Lipeng, Profir Irina, Jackstell Ralf, Franke Robert, Beller Matthias: Towards the Development of a Selective Ruthenium-Catalyzed Hydroformylation of Olefins. Chem. Eur. J. 2013, 19, 10589. <http://dx.doi.org/10.1002/chem.201300899>
  • Moran Joseph, Krische Michael J.: ChemInform Abstract: Formation of C-C Bonds via Ruthenium-Catalyzed Transfer Hydrogenation. ChemInform 2013, 44, no. <http://dx.doi.org/10.1002/chin.201309226>
  • Nicklaus Céline M., Minnaard Adriaan J., Feringa Ben L., de Vries Johannes G.: Synthesis of Renewable Fine-Chemical Building Blocks by Reductive Coupling between Furfural Derivatives and Terpenes. ChemSusChem 2013, 6, 1631. <http://dx.doi.org/10.1002/cssc.201300179>
  • Wu Lipeng, Fleischer Ivana, Jackstell Ralf, Beller Matthias: Efficient and Regioselective Ruthenium-catalyzed Hydro-aminomethylation of Olefins. J. Am. Chem. Soc. 2013, 135, 3989. <http://dx.doi.org/10.1021/ja312271c>
  • Geary Laina M., Glasspoole Ben W., Kim Mary M., Krische Michael J.: Successive C–C Coupling of Dienes to Vicinally Dioxygenated Hydrocarbons: Ruthenium Catalyzed [4 + 2] Cycloaddition across the Diol, Hydroxycarbonyl, or Dione Oxidation Levels. J. Am. Chem. Soc. 2013, 135, 3796. <http://dx.doi.org/10.1021/ja400691t>
  • Gao Xin, Woo Sang Kook, Krische Michael J.: Total Synthesis of 6-Deoxyerythronolide B via C–C Bond-Forming Transfer Hydrogenation. J. Am. Chem. Soc. 2013, 135, 4223. <http://dx.doi.org/10.1021/ja4008722>
  • Murphy Stephen K., Dong Vy M.: Enantioselective Ketone Hydroacylation Using Noyori’s Transfer Hydrogenation Catalyst. J. Am. Chem. Soc. 2013, 135, 5553. <http://dx.doi.org/10.1021/ja4021974>
  • Del Valle David J., Krische Michael J.: Total Synthesis of (+)-Trienomycins A and F via C–C Bond-Forming Hydrogenation and Transfer Hydrogenation. J. Am. Chem. Soc. 2013, 135, 10986. <http://dx.doi.org/10.1021/ja4061273>
  • Park Boyoung Y., Montgomery T. Patrick, Garza Victoria J., Krische Michael J.: Ruthenium Catalyzed Hydrohydroxyalkylation of Isoprene with Heteroaromatic Secondary Alcohols: Isolation and Reversible Formation of the Putative Metallacycle Intermediate. J. Am. Chem. Soc. 2013, 135, 16320. <http://dx.doi.org/10.1021/ja4087193>
  • McInturff Emma L., Mowat Jeffrey, Waldeck Andrew R., Krische Michael J.: Ruthenium-Catalyzed Hydrohydroxyalkylation of Acrylates with Diols and α-Hydroxycarbonyl Compounds To Form Spiro- and α-Methylene-γ-butyrolactones. J. Am. Chem. Soc. 2013, 135, 17230. <http://dx.doi.org/10.1021/ja410533y>
  • Shen Kun, Han Xiuling, Lu Xiyan: Cationic Pd(II)-Catalyzed Reductive Cyclization of Alkyne-Tethered Ketones or Aldehydes Using Ethanol as Hydrogen Source. Org. Lett. 2013, 15, 1732. <http://dx.doi.org/10.1021/ol400531a>
  • Chen Te-Yu, Krische Michael J.: Regioselective Ruthenium Catalyzed Hydrohydroxyalkylation of Dienes with 3-Hydroxy-2-oxindoles: Prenylation, Geranylation, and Beyond. Org. Lett. 2013, 15, 2994. <http://dx.doi.org/10.1021/ol401184k>
  • Sam Brannon, Montgomery T. Patrick, Krische Michael J.: Ruthenium Catalyzed Reductive Coupling of Paraformaldehyde to Trifluoromethyl Allenes: CF3-Bearing All-Carbon Quaternary Centers. Org. Lett. 2013, 15, 3790. <http://dx.doi.org/10.1021/ol401771a>
  • Jeso Valer, Micalizio Glenn C.: Asymmetric synthesis: Relay catalysis at a boron centre. Nature 2013, 494, 179. <http://dx.doi.org/10.1038/494179a>
  • Schmitt Daniel C., Lee Jungyong, Dechert-Schmitt Anne-Marie R., Yamaguchi Eiji, Krische Michael J.: Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: byproduct-free prenylation of hydantoins. Chem. Commun. 2013, 49, 6096. <http://dx.doi.org/10.1039/c3cc43463j>
  • Leung Joyce C., Geary Laina M., Chen Te-Yu, Zbieg Jason R., Krische Michael J.: Direct, Redox-Neutral Prenylation and Geranylation of Secondary Carbinol C–H Bonds: C4-Regioselectivity in Ruthenium-Catalyzed C–C Couplings of Dienes to α-Hydroxy Esters. J. Am. Chem. Soc. 2012, 134, 15700. <http://dx.doi.org/10.1021/ja3075049>
  • McInturff Emma L., Yamaguchi Eiji, Krische Michael J.: Chiral-Anion-Dependent Inversion of Diastereo- and Enantioselectivity in Carbonyl Crotylation via Ruthenium-Catalyzed Butadiene Hydrohydroxyalkylation. J. Am. Chem. Soc. 2012, 134, 20628. <http://dx.doi.org/10.1021/ja311208a>