Pd-catalyzed α-arylation of α,α-difluoroketones with aryl bromides and chlorides. A route to difluoromethylarenes

Journal of the American Chemical Society

Volumn 136, Issue 11, 2014, Pages 4149-4152

  Ge, Shaozhong ^a   Chaładaj, Wojciech ^a   Hartwig, John F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHLORINE COMPOUNDS; METAL HALIDES;

ARYL BROMIDES; ARYL HALIDES; ARYLATIONS; AS-LIGANDS; C-C BONDS; HIGH YIELD; ONE POT; TWO-STEP PROCEDURE;

CATALYSIS;

ALKYL GROUP; BROMINE DERIVATIVE; CHLORIDE; FLUOROMETHANE; KETONE DERIVATIVE; ORGANIC COMPOUND; PALLADIUM;

ARTICLE; ARYLATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; SYNTHESIS;

CATALYSIS; HYDROCARBONS, BROMINATED; HYDROCARBONS, CHLORINATED; HYDROCARBONS, FLUORINATED; KETONES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84896515832     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501117v     Document Type: Article

References (24)

1. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
2. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432
3. Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Compounds: Principles and Commercial Applications; Plenum: New York, 2000.
4. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2013.
5. Feng, Z.; Min, Q.-Q.; Xiao, Y.-L.; Zhang, B.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 1669
6. Enchavarren, A. M.; Cárdenas, D. J. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2008; Vol. 1, p 1.
7. Zemtsov, A. A.; Kondratyev, N. S.; Levin, V. V.; Struchkova, M. I.; Dilman, A. D. J. Org. Chem. 2013, 79, 818
8. Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560
9. Guo, C.; Wang, R.-W.; Qing, F.-L. J. Fluorine Chem. 2012, 143, 135
10. Guo, Y.; Shreeve, J. n. M. Chem. Commun. 2007, 3583
11. Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073
12. Bruno, N. C.; Buchwald, S. L. Org. Lett. 2013, 15, 2876
13. Bruno, N. C.; Tudge, M. T.; Buchwald, S. L. Chem. Sci. 2013, 4, 916
14. Aráoz, R.; Anhalt, E.; René, L.; Badet-Denisot, M.-A.; Courvalin, P.; Badet, B. Biochemistry 2000, 39, 15971
15. Hope, H. R. J. Lipid Res. 2000, 41, 1604
16. Markovskij, L. N.; Pashinnik, V. E.; Kirsanov, A. V. Synthesis 1973, 787
17. Middleton, W. J. J. Org. Chem. 1975, 40, 574
18. Dolbier, W. R.; Xie, P.; Zhang, L.; Xu, W.; Chang, Y.; Abboud, K. A. J. Org. Chem. 2008, 73, 2469
19. Fujikawa, K.; Kobayashi, A.; Amii, H. Synthesis 2012, 44, 3015
20. Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494
21. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 5524
22. Prakash, G. K. S.; Ganesh, S. K.; Jones, J.-P.; Kulkarni, A.; Masood, K.; Swabeck, J. K.; Olah, G. A. Angew. Chem., Int. Ed. 2012, 51, 12090
23. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644
24. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679