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Carbonylative Heck Reaction

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Abstract

Carbonylative transition metal catalysis has since the pioneering work performed by Heck and coworkers in the early 1970s evolved into a highly attractive strategy for the incorporation of the carbonyl unit using mild reaction conditions [1, 2]. The introduction of the highly versatile CO moiety not only elongates the expanding molecule with a one carbon fragment, but may also serve as a flexible platform for further manipulations of the molecule displaying numerous applications. Otherwise, the carbonyl entity may also act as a valuable motif in itself and is found in a vast number of bioactive compounds.

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References

  1. Schoenberg A, Bartoletti I, Heck RF (1974) J Org Chem 39:3318

    Article  CAS  Google Scholar 

  2. Grigg R, Mutton SP (2010) Tetrahedron 66:5515

    Article  CAS  Google Scholar 

  3. Brennführer A, Neumann H, Beller M (2009) Angew Chem Int Ed 48:4114

    Article  Google Scholar 

  4. Wu X-F, Jiao H, Neumann H, Beller M (2011) ChemCatChem 3:726

    Article  CAS  Google Scholar 

  5. Munday RH, Martinelli JR, Buchwald SL (2008) J Am Chem Soc 130:2754

    Article  CAS  Google Scholar 

  6. Arthuis M, Lecup A, Roulland E (2010) Chem Commun 46:7810

    Article  CAS  Google Scholar 

  7. Kolla L (ed) (2008) Modern carbonylation methods. Wiley and Sons, Germany

    Google Scholar 

  8. Roberts B, Liptrot D, Alcaraz L, Luker T, Stocks M (2010) J Org Lett 12:4280

    Article  CAS  Google Scholar 

  9. Wu X, Wannberg J, Larhed M (2006) Tetrahedron 62:4665

    Article  CAS  Google Scholar 

  10. Amatore C, Jutand A (2000) Acc Chem Res 33:314

    Article  CAS  Google Scholar 

  11. Carrow BP, Hartwig JF (2010) J Am Chem Soc 132:79

    Article  CAS  Google Scholar 

  12. Henriksen ST, Norrby P-O, Kaukoranta P, Andersson PG (2008) J Am Chem Soc 130:10414

    Article  CAS  Google Scholar 

  13. Satoh T, Itaya T, Okuro K, Miura M, Nomura M (1995) J Org Chem 60:7267

    Article  CAS  Google Scholar 

  14. Wu X-F, Neumann H, Beller M (2010) Angew Chem Int Ed 49:5284

    Article  CAS  Google Scholar 

  15. Wu X-F, Jiao H, Neumann H, Beller M (2011) ChemCatChem 3:726

    Article  CAS  Google Scholar 

  16. Wu X-F, Neumann H, Spannenberg A, Schulz T, Jiao H, Beller M (2010) J Am Chem Soc 132:14596

    Article  CAS  Google Scholar 

  17. Martinelli JR, Watson DA, Freckmann DMM, Barder TE, Buchwald SL (2008) J Org Chem 73:7102

    Google Scholar 

  18. Fujita T, Nakano K, Yamashita M, Nozaki K (2006) J Am Chem Soc 128:1968

    Article  CAS  Google Scholar 

  19. Gaviño R, Pellegrini S, Castanet Y, Mortreux A, Mentré O (2001) App Catal A General 217:91

    Article  Google Scholar 

  20. Sergeev AG, Spannenberg A, Beller M (2008) J Am Chem Soc 130:15549

    Article  CAS  Google Scholar 

  21. Hermange P, Lindhardt AT, Taaning RH, Bjerglund K, Lupp D, Skrydstrup T (2011) J Am Chem Soc 133:6061

    Article  CAS  Google Scholar 

  22. Gauthier D, Lindhardt AT, Olsen EPK, Overgaard J, Skrydstrup T (2010) J Am Chem Soc 132:7998

    Article  CAS  Google Scholar 

  23. Martins A, Candito DA, Lautens M (2010) Org Lett 12:5186

    Article  CAS  Google Scholar 

  24. Klaus S, Neumann H, Zapf A, Strübing D, Hübner S, Almena J, Riermeier T, Gross P, Sarich M, Krahnert W-R, Rossen K, Beller M (2006) Angew Chem Int Ed 45:154

    Article  CAS  Google Scholar 

  25. Ishiyama T, Kizaki H, Hayashi T, Suzuki A, Miyaura N (1998) J Org Chem 63:4726

    Article  CAS  Google Scholar 

  26. Garrou PE, Heck RF (1976) J Am Chem Soc 98:4115

    Article  CAS  Google Scholar 

  27. Cao P, Sun Y, Gu R (2004) J Phys Chem B 108:4716

    Article  CAS  Google Scholar 

  28. Veleckis E, Hacker DS (1984) J Chem Eng Data 29:36

    Article  CAS  Google Scholar 

Download references

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Correspondence to Thomas Meyer Gøgsig .

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© 2012 Springer-Verlag Berlin Heidelberg

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Gøgsig, T.M. (2012). Carbonylative Heck Reaction. In: New Discoveries on the β-Hydride Elimination. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32099-6_7

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