Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1476-1479

  Wotal, Alexander C ^a   Weix, Daniel J ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; ESTER; HALOGENATED HYDROCARBON; KETONE; NICKEL; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; ESTERS; HYDROCARBONS, HALOGENATED; KETONES; MOLECULAR STRUCTURE; NICKEL; OXIDATION-REDUCTION; PYRIDINES;

EID: 84858677128     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300217x     Document Type: Article

References (39)

1. Dieter, R. K. Tetrahedron 1999, 55, 4177
2. Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1998, 1739
3. Singh, J.; Satyamurthi, N.; Aidhen, I. J. Prakt. Chem. 2000, 342, 340
4. Stephanopoulos, N.; Francis, M. B. Nat. Chem. Biol. 2011, 7, 876
5. Kalia, J.; Raines, R. T. Curr. Org. Chem. 2010, 14, 138
6. Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974
7. An alternative strategy is the use of functionalized RMgX: Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943
8. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636
9. Li, H.; Yang, H.; Liebeskind, L. S. Org. Lett. 2008, 10, 4375
10. Sato, T.; Naruse, K.; Enokiya, M.; Fujisawa, T. Chem. Lett. 1981, 10, 1135
11. Negishi, E.-i.; Bagheri, V.; Chatterjee, S.; Luo, F.-T.; Miller, J. A.; Stoll, A. T. Tetrahedron Lett. 1983, 24, 5181
12. Tamaru, Y.; Ochiai, H.; Sanda, F.; Yoshida, Z.-i. Tetrahedron Lett. 1985, 26, 5529
13. Harada, T.; Kotani, Y.; Katsuhira, T.; Oku, A. Tetrahedron Lett. 1991, 32, 1573
14. Asaoka, M.; Kosaka, A.; Tanaka, M.; Ueda, T.; Houkawa, T.; Takei, H. J. Chem. Soc., Perkin Trans. 1 1997, 2949
15. Wang, D.; Zhang, Z. Org. Lett. 2003, 5, 4645
16. Yus, M.; Ortiz, R. Eur. J. Org. Chem. 2004, 2004, 3833
17. Fukuyama, T.; Tokuyama, H. Aldrichimica Acta 2005, 37, 87
18. Mori, Y.; Seki, M. Adv. Synth. Catal. 2007, 349, 2027
19. Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964
20. Tatamidani, H.; Kakiuchi, F.; Chatani, N. Org. Lett. 2004, 6, 3597
21. Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554
22. Zhang, Z.; Lindale, M. G.; Liebeskind, L. S. J. Am. Chem. Soc. 2011, 133, 6403
23. Schmink, J. R.; Krska, S. W. J. Am. Chem. Soc. 2011, 133, 19574
24. Habeeb, J. J.; Tuck, D. G. Chem. Commun. 1976, 696
25. Shono, T.; Nishiguchi, I.; Ohmizu, H. Chem. Lett. 1977, 6, 1021
26. Onaka, M.; Matsuoka, Y.; Mukaiyama, T. Chem. Lett. 1981, 10, 531
27. d'Incan, E.; Sibille, S.; Périchon, J.; Moingeon, M.-O.; Chaussard, J. Tetrahedron Lett. 1986, 27, 4175
28. Marzouk, H.; Rollin, Y.; Folest, J. C.; Nédélec, J. Y.; Périchon, J. J. Organomet. Chem. 1989, 369, C47
29. Amatore, C.; Jutand, A.; Périchon, J.; Rollin, Y. Monatsh. Chem. 2000, 131, 1293
30. Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920
31. Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 46, 5743
32. Shrestha, R.; Weix, D. J. Org. Lett. 2011, 13, 2766
33. Eichman, C. C.; Stambuli, J. P. J. Org. Chem. 2009, 74, 4005
34. Kobayashi, S.; Iimori, T.; Izawa, T.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 2406
35. Tsai, C.-S.; Liu, P.-Y.; Yen, H.-Y.; Hsu, T.-L.; Wong, C.-H. Chem. Commun. 2010, 46, 5575
36. Adam, G. C.; Sorensen, E. J.; Cravatt, B. F. Mol. Cell. Proteomics 2002, 1, 828
37. For a summary of the utility of biotin conjugates, the challenges associated with hydrolysis of amide linkers, and the synthesis of a biotin-derived alkyne without an amide or ester likange, see: Corona, C.; Bryant, B. K.; Arterburn, J. B. Org. Lett. 2006, 8, 1883
38. Yamamoto, T.; Kohara, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1981, 54, 2010
39. Yamamoto, T.; Kohara, T.; Osakada, K.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1983, 56, 2147