Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 12018-12032

  Skillinghaug, Bobo ^a   Sköld, Christian ^a   Rydfjord, Jonas ^a   Svensson, Fredrik ^a   Behrends, Malte ^a   Sävmarker, Jonas ^a   Sjöberg, Per J R ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; CARBOXYLATION; CATALYSIS; CATALYTIC OXIDATION; CYANIDES; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY IONIZATION; FREE ENERGY; KETONES; MASS SPECTROMETRY; MICROWAVE IRRADIATION; SODIUM; SYNTHESIS (CHEMICAL);

CATALYTIC CYCLES; DFT CALCULATION; EFFICIENT PROTOCOLS; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; ENERGY REQUIREMENTS; MECHANISTIC STUDIES; PALLADIUM INTERMEDIATES; REACTION MECHANISM;

PALLADIUM COMPOUNDS;

BENZOIC ACID DERIVATIVE; KETONE; NITRILE; PALLADIUM; SODIUM; SODIUM ARYLSULFINATE; UNCLASSIFIED DRUG; SULFINIC ACID DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECARBOXYLATION; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY MASS SPECTROMETRY; ENERGY; HYDROLYSIS; MICROWAVE IRRADIATION; REACTION ANALYSIS; SYNTHESIS; CATALYSIS; CHEMISTRY; QUANTUM THEORY;

CATALYSIS; KETONES; MOLECULAR STRUCTURE; NITRILES; PALLADIUM; QUANTUM THEORY; SODIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFINIC ACIDS;

EID: 84919658673     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501875n     Document Type: Article

References (68)

1. Odell, L. R.; Sävmarker, J.; Lindh, J.; Nilsson, P.; Larhed, M. Comprehensive Organic Synthesis II; Elsevier: Amsterdam, 2014; pp 492-537.
2. Molander, G.; Ellis, N. Acc. Chem. Res. 2007, 40, 275-286.
3. Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17-27.
4. Lindh, J.; Enquist, P.-A.; Pilotti, A˚.; Nilsson, P.; Larhed, M. J. Org. Chem. 2007, 72, 7957-7962.
5. Nordqvist, A.; Björkelid, C.; Andaloussi, M.; Jansson, A. M.; Mowbray, S. L.; Karlén, A.; Larhed, M. J. Org. Chem. 2011, 76, 8986-8998.
6. Sävmarker, J.; Lindh, J.; Nilsson, P.; Sjöberg, P. J. R.; Larhed, M. ChemistryOpen 2012, 1, 140-146.
7. Fardost, A.; Lindh, J.; Sjöberg, P. J. R.; Larhed, M. Adv. Synth. Catal. 2014, 356, 870-878.
8. Rydfjord, J.; Svensson, F.; Trejos, A.; Sjöberg, P. J. R.; Sköld, C.; Sävmarker, J.; Odell, L. R.; Larhed, M. Chem. - Eur. J. 2013, 19, 13803-13810.
9. Lindh, J.; Sjöberg, P. J. R.; Larhed, M. Angew. Chem. 2010, 49, 7733-7737.
10. Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030-5048.
11. Svensson, F.; Mane, R.; Sävmarker, J.; Larhed, M.; Sköld, C. Organometallics 2013, 7, 1-8.
12. Garves, K. J. Org. Chem. 1970, 35, 3273-3275.
13. Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238-3239.
14. Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 67, 9276-9287.
15. Tian, Q.; Pletnev, A. A.; Larock, R. C. J. Org. Chem. 2003, 68, 339-347.
16. Zhao, L.; Lu, X. Angew. Chem. 2002, 114, 4519-4521.
17. Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302-2303.
18. Zhao, B.; Lu, X. Org. Lett. 2006, 8, 5987-5990.
19. Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3551-3558.
20. Behrends, M.; Sävmarker, J.; Sjöberg, P. J. R.; Larhed, M. ACS Catal. 2011, 1, 1455-1459.
21. Miao, T.; Wang, G.-W. Chem. Commun. 2011, 47, 9501-9503.
22. Liu, J.; Zhou, X.; Rao, H.; Xiao, F.; Li, C.-J.; Deng, G.-J. Chem. - Eur. J. 2011, 17, 7996-7999.
23. Rao, B.; Zhang, W.; Hu, L.; Luo, M. Green Chem. 2012, 14, 3436.
24. Liu, B.; Guo, Q.; Cheng, Y.; Lan, J.; You, J. Chem. - Eur. J. 2011, 17, 13415-13419.
25. Ortgies, D.; Forgione, P. Synlett 2013, 24, 1715-1721.
26. Ortgies, D.; Barthelme, A.; Aly, S.; Desharnais, B.; Rioux, S.; Forgione, P. Synthesis 2013, 45, 694-702.
27. Colomb, J.; Billard, T. Tetrahedron Lett. 2013, 54, 1471-1474.
28. Zhou, C.; Liu, Q.; Li, Y.; Zhang, R. J. Org. Chem. 2012, 77, 10468-10472.
29. Cheng, K.; Hu, S.; Zhao, B. J. Org. Chem. 2013, 78, 5022-5025.
30. Wang, G.-W.; Miao, T. Chem. - Eur. J. 2011, 17, 5787-5790.
31. Zhou, X.; Luo, J.; Liu, J.; Peng, S.; Deng, G.-J. Org. Lett. 2011, 13, 1432-1435.
32. Hu, S.; Xia, P.; Cheng, K.; Qi, C. Appl. Organomet. Chem. 2013, 27, 188-190.
33. Bal Raju, K.; Mari, V.; Nagaiah, K. Synthesis 2013, 45, 2867-2874.
34. Wang, H.; Li, Y.; Zhang, R.; Jin, K.; Zhao, D.; Duan, C. J. Org. Chem. 2012, 77, 4849-4953.
35. Chen, W.; Zhou, X.; Xiao, F.; Luo, J.; Deng, G.-J. Tetrahedron Lett. 2012, 53, 4347-4350.
36. Liu, S.; Bai, Y.; Cao, X.; Xiao, F.; Deng, G.-J. Chem. Commun. 2013, 49, 7501-7503.
37. Chen, R.; Liu, S.; Liu, X.; Yang, L.; Deng, G.-J. Org. Biomol. Chem. 2011, 9, 7675-7679.
38. Wang, M.; Li, D.; Zhou, W.; Wang, L. Tetrahedron 2012, 68, 1926-1930.
39. Wu, M.; Luo, J.; Xiao, F.; Zhang, S.; Deng, G.-J.; Luo, H.-A. Adv. Synth. Catal. 2012, 354, 335-340.
40. Miao, T.; Li, P.; Wang, G.-W.; Wang, L. Chem. - Asian J. 2013, 8, 3185-3190.
41. Miao, T.; Wang, L. Adv. Synth. Catal. 2014, 356, 429-436.
42. Harris, L.; Parry, J.; Greifenstein, F. Anesthesiology 1956, 17, 648-652.
43. Markello, R.; King, B. Anesthesiology 1966, 27, 20-23.
44. Yelnosky, J.; Katz, R.; Dietrich, E. Toxicol. Appl. Pharmacol. 1964, 6, 37-47.
45. Pal Singh, I.; Bharate, S. B. Nat. Prod. Rep. 2006, 23, 558-591.
46. Picinelli, A.; Dapena, E.; Mangas, J. J. Agric. Food Chem. 1995, 43, 2273-2278.
47. Fukuhara, Y.; Yoshida, D. Agric. Biol. Chem. 1987, 51, 1441-1442.
48. Xue, L.; Su, W.; Lin, Z. Dalton Trans. 2010, 39, 9815-9822.
49. Zhang, S.-L.; Fu, Y.; Shang, R.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638-646.
50. Strauss, C.; Trainor, R. Aust. J. Chem. 1995, 48, 1665.
51. Kappe, C. O. Chem. Soc. Rev. 2013, 42, 4977-4990.
52. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727.
53. Rydfjord, J.; Svensson, F.; Fagrell, M.; Sävmarker, J.; Thulin, M.; Larhed, M. Beilstein J. Org. Chem. 2013, 9, 2079-2087.
54. Chen, W.; Li, P.; Miao, T.; Meng, L.-G.; Wang, L. Org. Biomol. Chem. 2013, 11, 420-424.
55. O'Connor Sraj, L.; Khairallah, G. N.; da Silva, G.; O'Hair, R. A. J. Organometallics 2012, 31, 1801-1807.
56. Vikse, K. L.; Ahmadi, Z.; McIndoe, J. S. Coord. Chem. Rev. 2014, 279, 96-114.
57. Enquist, P.-A.; Nilsson, P.; Sjöberg, P.; Larhed, M. J. Org. Chem. 2006, 71, 8779-8786.
58. Svennebring, A.; Sjöberg, P. J. R.; Larhed, M.; Nilsson, P. Tetrahedron 2008, 64, 1808-1812.
59. Curti, C.; Laget, M.; Carle, A. O.; Gellis, A.; Vanelle, P. Eur. J. Med. Chem. 2007, 42, 880-884.
60. Jaguar, version 7.6; Schrödinger LLC: New York, 2009.
61. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
62. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
63. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
64. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
65. Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11775-11788.
66. Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Honig, B.; Ringnalda, M.; Goddard, W. A. J. Am. Chem. Soc. 1994, 116, 11875-11882.
67. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.
68. Goodman, J. M.; Silva, M. Tetrahedron Lett. 2003, 44, 8233-8236.