Synlett 2013; 24(15): 1877-1881
DOI: 10.1055/s-0033-1339669
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© Georg Thieme Verlag Stuttgart · New York

[Pd(NHC)(PR3)] Complexes: Versatile Tools for Tandem Dehydrogenation–Hydrogenation Processes

Olivier Songis
EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK   Fax: +44(0)1334463808   Email: cc111@st-andrews.ac.uk
,
Catherine S. J. Cazin*
EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK   Fax: +44(0)1334463808   Email: cc111@st-andrews.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 28 June 2013

Accepted after revision: 01 August 2013

Publication Date:
23 August 2013 (online)

Abstract

Homogeneous Pd(0) complexes are powerful tools for numerous catalytic reactions. Recent work has demonstrated the unique properties displayed by [Pd(NHC)(PR3)] catalysts in the activation of ammonia borane (AB) and formic acid, with the subsequent formation of hydrogen. An understanding of the mechanism allowed for the design of a new dehydrogenation–hydrogenation tandem process using ‘hydrogen storage materials’. The hydrogenations of alkenes and alkynes were successfully performed at low catalyst loadings of Pd(0) species and mild conditions. Such tandem process represents a safe and innovative alternative to classic hydrogenation protocols.

 
  • References

    • 2a Diebolt O, Braunstein P, Nolan SP, Cazin CS. J. Chem. Commun. 2008; 3190
    • 2b Schmid TE, Jones DC, Songis O, Diebolt O, Furst MR. L, Slawin AM. Z, Cazin CS. J. Dalton Trans. 2013; 42: 7345
    • 2c Chartoire A, Lesieur M, Falivene L, Slawin AM. Z, Cavallo L, Cazin CS. J, Nolan SP. Chem. Eur. J. 2012; 18: 4517
    • 2d Diebolt O, Jurcik V, Correa da Costa R, Braunstein P, Cavallo L, Nolan SP, Slawin AM. Z, Cazin CS. J. Organometallics 2010; 29: 1443
  • 3 Hartmann CE, Nolan SP, Cazin CS. J. Organometallics 2009; 28: 2915
  • 4 Tessin UI, Bantreil X, Songis O, Cazin CS. J. Eur. J. Inorg. Chem. 2013; 12: 2007
  • 5 Akzinnay S, Bisaro F, Cazin CS. J. Chem. Commun. 2009; 5752
  • 6 Fantasia SNolan S. P. Chem. Eur. J. 2008; 14: 6987

    • For recent reviews on palladium-catalyzed hydrogenation, see:
    • 7a Chen Q.-A, Ye Z.-S, Duan Y, Zhou Y.-G. Chem. Soc. Rev. 2013; 42: 497
    • 7b Sumner CJr, Burchett W. Top. Catal. 2012; 55480
    • 7c Kirkorian K, Ellis A, Twyman LJ. Chem. Soc. Rev. 2012; 41: 6138
    • 7d Wang DS, Chen QA, Lu SM, Zhou YG. Chem. Rev. 2012; 112: 2557
    • 7e Hu X.-P, Wang D.-S, Yu C.-B, Zhou Y.-G, Zheng Z In Top. Organomet. Chem. Vol. 36. Ma S. Springer; Berlin: 2011: 313-354
    • 7f Oosthuizen RS, Nyamori VO. Platinum Met. Rev. 2011; 55: 154
    • 7g Xie J.-H, Zhu S.-F, Zhou Q.-L. Chem. Rev. 2011; 111: 1713
    • 7h Frost CG, Mutton L. Green Chem. 2010; 12: 1687
    • 8a Arnold PL, Cloke GN, Geldbach T, Hitchcock PB. Organometallics 1999; 18: 3228
    • 8b Sprengers JW, Wassenaar J, Clement ND, Cavell KJ, Elsevier CJ. Angew. Chem. Int. Ed. 2005; 44: 2026
    • 8c Hauwert P, Maestri G, Sprengers JW, Catellani M, Elsevier CJ. Angew. Chem. Int. Ed. 2008; 47: 3223
  • 9 Jurčík V, Nolan SP, Cazin CS. J. Chem. Eur. J. 2009; 15: 2509
  • 10 Fantasia S, Egbert JD, Jurčík V, Cazin CS. J, Jacobsen H, Cavallo L, Heinekey DM, Nolan SP. Angew. Chem. Int. Ed. 2009; 48: 5182
    • 11a Coontz R, Hanson B. Science 2004; 305: 957
    • 11b Crabtree GW, Dresselhaus MS. MRS Bull. 2008; 33: 421
  • 12 Hartmann CE, Jurčík V, Songis O, Cazin CS. J. Chem. Commun. 2013; 49: 1005
  • 13 Broggi J, Jurčík V, Songis O, Poater A, Cavallo L, Slawin AM. Z, Cazin CS. J. J. Am. Chem. Soc. 2013; 135: 4588