Palladium catalyzed carbonylative Heck reaction affording monoprotected 1,3-ketoaldehydes

Organic Letters

Volumn 14, Issue 10, 2012, Pages 2536-2539

  Gøgsig, Thomas M ^a   Nielsen, Dennis U ^a   Lindhardt, Anders T ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBON; CARBON MONOXIDE; IODINATED HYDROCARBON; KETONE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALDEHYDES; CARBON ISOTOPES; CARBON MONOXIDE; CATALYSIS; HYDROCARBONS, IODINATED; KETONES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84862085549     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300837d     Document Type: Article

References (34)

1. Larock, R. C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2 nd ed.; VCH: New York, 1999, and references cited therein.
2. Mackenzie, K. In The Chemistry of Alkenes; Patai, S., Ed.; Wiley: New York, 1964.
3. Kricheldorf, H. R.; Nuyken, O.; Swift, G. In Handbook of Polymer Synthesis, 2 nd ed.; Marcel Dekker: New York, 2005.
4. Handbook of Metathesis, Vols. 1-3; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
5. Hartwig, J. F. In Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: 2010.
6. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
7. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. 1994, 33, 2379
8. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945
9. Cabri, W.; Candiani, I.; Bedeschi, A. J. Org. Chem. 1990, 55, 3654
10. Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2
11. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176
12. Schnyder, A.; Aemmer, T.; Indolese, A. F.; Pittelkow, U.; Studer, M. Adv. Synth. Catal. 2002, 344, 495
13. Fristrup, P.; Quement, S. L.; Tanner, D.; Norrby., P.-O. Organometallics 2004, 23, 6160
14. Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751
15. Ruan, J.; Iggo, J. A.; Berry, N. G.; Xiao, J. J. Am. Chem. Soc. 2010, 132, 16689
16. Ruan, J.; Xiao, J. Acc. Chem. Res. 2011, 44, 614
17. Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 79
18. Datta, G. K.; von Schenk, H.; Hallberg, A.; Larhed, M. J. Org. Chem. 2006, 71, 3896
19. Wu, X.-F.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 5284
20. Wu, X.-F.; Neumann, H.; Spannenberg, A.; Schulz, T.; Jiao, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 14596
21. 2). See: Schranck, J.; Wu, X.-F.; Neumann, H.; Beller, M. Chem.-Eur. J. 2012, 18, 4827
22. Barnard, C. F. J. Org. Process Res. Dev. 2008, 12, 566
23. Kormos, C. M.; Leadbeater, N. E. Synlett 2007, 13, 2006
24. Gaviño, R.; Pellegrini, S.; Castanet, Y.; Mortreux, A.; Mentré, O. Appl. Catal., A 2001, 217, 91
25. Sergeev, A. G.; Spannenberg, A.; Beller, M. J. Am. Chem. Soc. 2008, 130, 15549
26. Alternatively, Hallberg and coworkers previously reported the palladium catalyzed regioselective β-aroylation of vinyl ethers using aroyl chlorides. See: Anderson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 4257
27. Hermange, P.; Gøgsig, T. M.; Lindhardt, A. T.; Taaning, R. H.; Skrydstrup, T. Org. Lett. 2011, 13, 2444
28. For the direct synthesis of 1,3-diketones starting from aryl iodides, see: Gøgsig, T. M.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. Angew. Chem., Int. Ed. 2012, 51, 798
29. Hermange, P.; Lindhardt, A. T.; Taaning, R. H.; Bjerglund, K.; Lupp, D.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 6061
30. Gürtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107
31. Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178
32. Gottumukkala, A. L.; de Vries, J. G.; Minnaard, A. J. Chem.-Eur. J. 2011, 17, 3091
33. Barrios-Landeros, F.; Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 8141
34. Garrou, P. E.; Heck, R. F. J. Am. Chem. Soc. 1976, 98, 4115