Literature DB >> 20119477

Efficient Dehydrogenation of Amines and Carbonyl Compounds Catalyzed by a Tetranuclear Ruthenium-mu-Oxo-mu-Hydroxo-Hydride Complex.

Chae S Yi1, Do W Lee.   

Abstract

The tetranuclear ruthenium-mu-oxo-mu-hydroxo-hydride complex {[(PCy(3))(CO)RuH](4)(mu(4)-O)(mu(3)-OH)(mu(2)-OH)} (1) was found to be a highly effective catalyst for the transfer dehydrogenation of amines and carbonyl compounds. For example, the initial turnover rate of the dehydrogenation of 2-methylindoline was measured to be 1.9 s(-1) with the TON of 7950 after 1 h at 200 degrees C. The extensive H/D scrambling patterns observed from the dehydrogenation reaction of indoline-N-d(1) and indoline-alpha-d(2) suggest a monohydride mechanistic pathway with the C-H bond activation rate-limiting step.

Entities:  

Year:  2009        PMID: 20119477      PMCID: PMC2658527          DOI: 10.1021/om8010883

Source DB:  PubMed          Journal:  Organometallics        ISSN: 0276-7333            Impact factor:   3.876


  11 in total

1.  C-H and C-C bond activation of primary amines through dehydrogenation and transimination.

Authors:  C H Jun; K Y Chung; J B Hong
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

2.  Thermally Stable Homogeneous Catalysts for Alkane Dehydrogenation S.O. thanks the German Academic Exchange Service (DAAD) for financing a research stay with W.C.K. in the USA. This work was supported by the National Science Foundation (CHE 9800184 to M.B.H.), by the University of California Energy Institute and University of California Santa Barbara (to W.C.K.), and by the German Research Association (DFG, to M.W.H). We thank Dr. R. Mynott and Mrs. C. Wirtz, MPI für Kohlenforschung, for NMR spectroscopic investigations.

Authors:  Matthias W. Haenel; Stephan Oevers; Klaus Angermund; William C. Kaska; Hua-Jun Fan; Michael B. Hall
Journal:  Angew Chem Int Ed Engl       Date:  2001-10-01       Impact factor: 15.336

3.  Dehydrogenation of aromatic amines to imines via ruthenium-catalyzed hydrogen transfer.

Authors:  Alida H Ell; Joseph S M Samec; Claudia Brasse; Jan-E Bäckvall
Journal:  Chem Commun (Camb)       Date:  2002-05-21       Impact factor: 6.222

4.  Mechanistic studies of the transfer dehydrogenation of cyclooctane catalyzed by iridium bis(phosphinite) p-XPCP pincer complexes.

Authors:  Inigo Göttker-Schnetmann; Maurice Brookhart
Journal:  J Am Chem Soc       Date:  2004-08-04       Impact factor: 15.419

5.  Catalytic alkane metathesis by tandem alkane dehydrogenation-olefin metathesis.

Authors:  Alan S Goldman; Amy H Roy; Zheng Huang; Ritu Ahuja; William Schinski; Maurice Brookhart
Journal:  Science       Date:  2006-04-14       Impact factor: 47.728

6.  On the mechanism of (PCP)Ir-catalyzed acceptorless dehydrogenation of alkanes: a combined computational and experimental study.

Authors:  Karsten Krogh-Jespersen; Margaret Czerw; Nadine Summa; Kenton B Renkema; Patrick D Achord; Alan S Goldman
Journal:  J Am Chem Soc       Date:  2002-09-25       Impact factor: 15.419

7.  Structural features of aliphatic N-nitrosamines of 7-azabicyclo[2.2.1]heptanes that facilitate N-NO bond cleavage.

Authors:  T Ohwada; M Miura; H Tanaka; S Sakamoto; K Yamaguchi; H Ikeda; S Inagaki
Journal:  J Am Chem Soc       Date:  2001-10-24       Impact factor: 15.419

8.  Novel synthesis of enamines by iridium-catalyzed dehydrogenation of tertiary amines.

Authors:  Xiawei Zhang; Amy Fried; Spencer Knapp; Alan S Goldman
Journal:  Chem Commun (Camb)       Date:  2003-08-21       Impact factor: 6.222

9.  Iridium bis(phosphinite) p-XPCP pincer complexes: highly active catalysts for the transfer dehydrogenation of alkanes.

Authors:  Inigo Göttker-Schnetmann; Peter White; Maurice Brookhart
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

10.  Highly Cooperative Tetrametallic Ruthenium-mu-Oxo-mu-Hydroxo Catalyst for the Alcohol Oxidation Reaction.

Authors:  Chae S Yi; Tonya N Zeczycki; Ilia A Guzei
Journal:  Organometallics       Date:  2006       Impact factor: 3.876

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  9 in total

1.  Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products.

Authors:  Andrei V Iosub; Shannon S Stahl
Journal:  ACS Catal       Date:  2016-10-24       Impact factor: 13.084

2.  Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols.

Authors:  Yusuke Izawa; Doris Pun; Shannon S Stahl
Journal:  Science       Date:  2011-06-09       Impact factor: 47.728

3.  Chain- and Regioselective Ethylene and Styrene Dimerization Reactions Catalyzed by a Well-Defined Cationic Ruthenium-Hydride Complex: New Insights on the Styrene Dimerization Mechanism.

Authors:  Do W Lee; Chae S Yi
Journal:  Organometallics       Date:  2010-01-01       Impact factor: 3.876

4.  Aerobic dehydrogenation of cyclohexanone to cyclohexenone catalyzed by Pd(DMSO)2(TFA)2: evidence for ligand-controlled chemoselectivity.

Authors:  Tianning Diao; Doris Pun; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-05-24       Impact factor: 15.419

5.  Aerobic dehydrogenation of cyclohexanone to phenol catalyzed by Pd(TFA)2/2-dimethylaminopyridine: evidence for the role of Pd nanoparticles.

Authors:  Doris Pun; Tianning Diao; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-05-24       Impact factor: 15.419

6.  Molecular ligand modulation of palladium nanocatalysts for highly efficient and robust heterogeneous oxidation of cyclohexenone to phenol.

Authors:  Teng Xue; Zhaoyang Lin; Chin-Yi Chiu; Yongjia Li; Lingyan Ruan; Gongming Wang; Zipeng Zhao; Chain Lee; Xiangfeng Duan; Yu Huang
Journal:  Sci Adv       Date:  2017-01-06       Impact factor: 14.136

7.  Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors.

Authors:  Jingwu Zhang; Qiangqiang Jiang; Dejun Yang; Xiaomei Zhao; Yanli Dong; Renhua Liu
Journal:  Chem Sci       Date:  2015-05-19       Impact factor: 9.825

8.  Synthesis of a molecularly defined single-active site heterogeneous catalyst for selective oxidation of N-heterocycles.

Authors:  Yujing Zhang; Shaofeng Pang; Zhihong Wei; Haijun Jiao; Xingchao Dai; Hongli Wang; Feng Shi
Journal:  Nat Commun       Date:  2018-04-13       Impact factor: 14.919

9.  Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism.

Authors:  Lin Huang; Alessandro Bismuto; Simon A Rath; Nils Trapp; Bill Morandi
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-25       Impact factor: 15.336

  9 in total

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