Sulfonyl Azides as Precursors in Ligand-Free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides

Journal of Organic Chemistry

Volumn 81, Issue 7, 2016, Pages 2681-2691

  Chow, Shiao Y ^a   Stevens, Marc Y ^a   Odell, Luke R ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; CARBONYLATION; CATALYSIS; METABOLISM; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PALLADIUM; SULFUR COMPOUNDS; UREA;

CHEMICAL EQUATIONS; EFFICIENT SYNTHESIS; NUCLEOPHILIC SUBSTITUTIONS; PALLADIUM CATALYZED CARBONYLATION; PALLADIUM-CATALYZED; SULFONYL AZIDES; SULFONYL ISOCYANATES; TWO-CHAMBER SYSTEMS;

CHELATION;

1 TOSYLPIPERIDINE; 4 ACETYL N BUTYLBENZENESULFONAMIDE; 4 METHYL N (PROP 2 YN 1 YL)BENZENESULFONAMIDE; 4 METHYL N (THIOPHEN 2 YLMETHYL)BENZENESULFONAMIDE; 5 {N BUTYLSULFAMOYL) 4 CHLORO 2 [(FURAN 2 YLMETHYL)AMINO]BENZOIC ACID; AZIDE; CARBAMIC ACID DERIVATIVE; LIGAND; METHYL 3 [(4 METHYLPHENYL)SULFONAMIDO]PROPANOATE; METHYL TOLUENESULFONYLGLYCINATE; N ALLYL 4 METHYLBENZENESULFONAMIDE; N BENZYL 4 METHYLBENZENESULFONAMIDE; N BUTYL 2 BROMOBENZENESULFONAMIDE; N BUTYL 4 BROMOBENZENESULFONAMIDE; N BUTYL 4 METHOXYBENZENESULFONAMIDE; N BUTYLBENZO[B]THIOPHENE 3 SULFONAMIDE; N BUTYLTHIOPHENE 2 SULFONAMIDE; N CYCLOHEXYL 4 METHYLBENZENESULFONAMIDE; N HEXYL 4 METHYLBENZENESULFONAMIDE; N,N DIETHYL 4 METHYLBENZENESULFONAMIDE; N,N DIPROPYL 4 METHYLBENZENESULFONAMIDE; PALLADIUM; SULFONAMIDE; SULFONYLUREA DERIVATIVE; TRIETHYLAMMONIUM METHYL 4 (3-TOSYLUREIDO)BENZOATE; TRIETHYLAMMONIUM N [(4 BROMOPHENYL)CARBAMOYL] 4 METHYLBENZENESULFONAMIDE; TRIETHYLAMMONIUM N [(4 CHLOROPHENYL)CARBAMOYL] 4 METHYLBENZENESULFONAMIDE; TRIETHYLAMMONIUM N [(4 CYANOPHENYL)CARBAMOYL] 4 METHYLBENZENESULFONAMIDE; TRIETHYLAMMONIUM N [(4 METHOXYPHENYL)CARBAMOYL] 4 METHYLBENZENESULFONAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

CARBONYLATION; CATALYSIS; DECOMPOSITION; DERIVATIZATION; DRUG STABILITY; DRUG SYNTHESIS; ELECTRON TRANSPORT; NUCLEOPHILICITY; REVIEW; SUBSTITUTION REACTION; SULFONATION;

EID: 84963611475     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02755     Document Type: Review

References (89)

1. Narasaiah, T.; Rao, D. S.; Rasheed, S.; Madhava, G.; Srinivasulu, D.; Brahma, P. Der. Pharm. Lett. 2012, 4, 854-862
2. Choi, S. H.; Quinti, L.; Kazantsev, A. G.; Silverman, R. B. Bioorg. Med. Chem. Lett. 2012, 22, 2789-2793 10.1016/j.bmcl.2012.02.089
3. Ceras, J.; Cirauqui, N.; Pérez-Silanes, S.; Aldana, I.; Monge, A.; Galiano, S. Eur. J. Med. Chem. 2012, 52, 1-13 10.1016/j.ejmech.2012.02.049
4. Howbert, J. J.; Grossman, C. S.; Crowell, T. A.; Rieder, B. J.; Harper, K. W.; Kramer, K. E.; Tao, K. V.; Aikins, J.; Poore, G. A. J. Med. Chem. 1990, 33, 2393-2407 10.1021/jm00171a013
5. Murugaiah, A. M. S.; Wu, X. Y.; Wallinder, C.; Mahalingam, A. K.; Wan, C.; Sköld, C.; Botros, M.; Alterman, M. J. Med. Chem. 2012, 55, 2265-2278 10.1021/jm2015099
6. Campbell, J. A.; Hart, D. J. J. Org. Chem. 1993, 58, 2900-2903 10.1021/jo00062a041
7. Neustadt, B. R. Tetrahedron Lett. 1994, 35, 379-380 10.1016/0040-4039(94)85058-5
8. Young, J. M.; Lee, A. G.; Chandrasekaran, R. Y.; Tucker, J. W. J. Org. Chem. 2015, 80, 8417-8423 10.1021/acs.joc.5b01287
9. Saczewski, F.; Kornicka, A.; Brzozowski, Z. Green Chem. 2006, 8, 647-656 10.1039/B604376C
10. Luckhurst, C. A.; Millichip, I.; Parker, B.; Reuberson, J.; Furber, M. Tetrahedron Lett. 2007, 48, 8878-8882 10.1016/j.tetlet.2007.10.046
11. Blank, B.; Farina, F.; Kerwin, J. F.; Saunders, H. J. Org. Chem. 1961, 26, 1551-1553 10.1021/jo01064a059
12. Mariella, R.; Jonauskas, R. J. Org. Chem. 1958, 23, 923 10.1021/jo01100a620
13. Perez, A. M.; Rossert, M.; Kresze, G. Eur. J. Med. Chem. 1981, 1981, 65-69 10.1002/jlac.198119810112
14. Beyer, E. M.; Duffy, M. J.; Hay, J. V.; Schlueter, D. D. Sulfonylureas in Herbicides. Chemistry, Degradation and Mode of Action; Marcel Dekker Inc., 1988.
15. Ková, M.; Sabatié, A.; Floch, L. ARKIVOC 2001, 100-108
16. Franz, J. A.; Osuch, C. J. Org. Chem. 1964, 29, 2592-2595 10.1021/jo01032a025
17. Arnswald, M.; Neumann, W. P. J. Org. Chem. 1993, 58, 7022-7028 10.1021/jo00077a020
18. Cervello, J.; Sastre, T. Synthesis 1990, 3, 221-222 10.1055/s-1990-26837
19. Ulrich, H.; Sayigh, A. A. R. Angew. Chem., Int. Ed. Engl. 1966, 5, 704 10.1002/anie.196607041
20. Ren, L.; Jiao, N. Chem. Commun. 2014, 50, 3706 10.1039/c4cc00538d
21. For reviews, see Gautam, P.; Bhanage, B. M. Catal. Sci. Technol. 2015, 5, 4663-4702 and references therein 10.1039/C5CY00691K
22. Åkerbladh, L.; Nordeman, P.; Wejdemar, M.; Odell, L. R.; Larhed, M. J. Org. Chem. 2015, 80, 1464-1471 10.1021/jo502400h
23. Xu, T.; Alper, J. J. Am. Chem. Soc. 2014, 136, 16970-16973 10.1021/ja508588b
24. Stevens, M. Y.; Sawant, R. T.; Odell, L. R. J. Org. Chem. 2014, 79, 4826-4831 10.1021/jo500553q
25. Kim, S. H.; Park, S. H.; Choi, J. H.; Chang, H. Chem.-Asian J. 2011, 6, 2618-2634 10.1002/asia.201100340
26. Culhane, J.; Fokin, V. Org. Lett. 2011, 13, 4578-4580 10.1021/ol201705k
27. Suárez, J. R.; Kwiczak, J.; Grenda, K.; Jimeno, M. L.; Chiara, J. L. Adv. Synth. Catal. 2013, 355, 913-918 10.1002/adsc.201201001
28. Lee, E.; Ryu, T.; Shin, E.; Son, J.-Y.; Choi, W.; Lee, P. H. Org. Lett. 2015, 17, 2470-2473 10.1021/acs.orglett.5b00977
29. Dianova, L.; Berseneva, V.; Beryozkina, T.; Efimov, I.; Kosterina, M.; Eltsov, O.; Dehaen, W.; Bakulev, V. Eur. J. Org. Chem. 2015, 2015, 6917-6913 10.1002/ejoc.201500968
30. Pi, C.; Cui, X.; Wu, Y. J. Org. Chem. 2015, 80, 7333-7339 10.1021/acs.joc.5b01377
31. Åberg, O.; Långström, B. J. Labelled Compd. Radiopharm. 2011, 54, 38-42 10.1002/jlcr.1803
32. Nordeman, P.; Odell, L. R.; Larhed, M. J. Org. Chem. 2012, 77, 11393-11398 10.1021/jo302322w
33. Zybill, C. E. Synthetic Methods of Organometallic and Inorganic Chemistry: Transition Metals, Part 2. In Synthetic Methods of Organometallic and Inorganic Chemistry: Transition Metals, Part 1-3; Herrman, W. A., Ed.; Thieme Verlag: New York, 1997; Vol. 8, p 59.
34. Hermange, P.; Lindhardt, A.; Taaning, R.; Bjerglund, K.; Lupp, D.; Skrydstrup, T. J. J. Am. Chem. Soc. 2011, 133, 6061-6071 10.1021/ja200818w
35. Berndt, D. C.; Faburada, A. L. J. Org. Chem. 1982, 47, 4167-4169 10.1021/jo00142a033
36. Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046-7 10.1021/ja056399e
37. Ruppel, J. V.; Kamble, R. M.; Zhang, X. P. Org. Lett. 2007, 9, 4889-4892 10.1021/ol702265h
38. Dong, K.; Fang, X.; Jackstell, R.; Beller, M. Chem. Commun. 2015, 51, 5059-5062 10.1039/C5CC00321K
39. Goddard-Borger, E. D.; Stick, R. V. Org. Lett. 2007, 9, 3797-800 10.1021/ol701581g
40. Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240 10.1002/anie.200400657
41. Organic Azides: Syntheses and Applications; Bräse, S.; Banert, K., Eds.; John Wiley & Sons, Ltd.: Chichester, UK, 2010.
42. Zhu, S. Tetrahedron Lett. 1992, 33, 6503-6504 10.1016/S0040-4039(00)79026-5
43. Zhu, S.; Jin, G.; He, P.; Xu, Y.; Huang, Q. Tetrahedron Lett. 2003, 44, 8717-8719 10.1016/j.tetlet.2003.09.174
44. Brouwer, A. J.; Merkx, R.; Dabrowska, K.; Rijkers, D. T. S.; Liskamp, R. M. J. Synthesis 2006, 2006, 455-460 10.1055/s-2006-926273
45. A stability assay was conducted on p -nitrobenzenesulfonyl chloride and p -nitrobenzenesulfonyl azide (see Figure S2, Supporting Information) to investigate the viability of sulfonyl azides as precursors for substituted sulfonamides.
46. Taylor, L. D.; Macdonald, R. J.; Rubin, L. E. J. Polym. Sci., Part A-1: Polym. Chem. 1971, 9, 3059-3061 10.1002/pol.1971.150091025
47. Casewit, C.; Roberts, J. D. J. Am. Chem. Soc. 1980, 102, 2364-2368 10.1021/ja00527a039
48. Barnard, C. F. J. Organometallics 2008, 27, 5402-5422 10.1021/om800549q
49. Yamamoto, A.; Ozawa, F.; Osakada, K.; Huang, L.; Son, T.; Kawasaki, N.; Doh, M.-K. Pure Appl. Chem. 1991, 63, 687-696 10.1351/pac199163050687
50. Ragaini, A. Dalt. Trans. 2009, 6251-6266 10.1039/b902425p
51. Díaz, D. J.; Darko, A. K.; McElwee-White, L. Eur. J. Org. Chem. 2007, 2007, 4453-4465 10.1002/ejoc.200700148
52. Li, W.; Wu, X.-F. Org. Lett. 2015, 17, 1910-1913 10.1021/acs.orglett.5b00603
53. Kang, T.; Kim, H.; Kim, J. G.; Chang, S. Chem. Commun. 2014, 50, 12073-12075 10.1039/C4CC05655H
54. Buathongjan, C.; Beukeaw, D.; Yotphan, S. Eur. J. Org. Chem. 2015, 2015, 1575-1582 10.1002/ejoc.201403531
55. Petersen, S. Chem. Ber. 1950, 83, 551-558 10.1002/cber.19500830609
56. Setliff, F. L.; Harrison, M. K. J. Ark. Acad. Sci. 2000, 54, 117-119
57. Bottari, F.; Mannelli, M.; Saettone, M. F. J. Pharm. Sci. 1970, 59, 1663-1666 10.1002/jps.2600591129
58. Tang, X.; Huang, L.; Qi, C.; Wu, X.; Wu, W.; Jiang, H. Chem. Commun. 2013, 49, 6102-6104 10.1039/c3cc41249k
59. Skita, A.; Rolfes, H. Ber. Dtsch. Chem. Ges. B 1920, 53, 1242-1255 10.1002/cber.19200530712
60. Groves, L. G.; Turner, E. E.; Sharp, G. I. J. Chem. Soc. 1929, 0, 512-524 10.1039/JR9290000512
61. Marckwald, W.; v. Droste-Huelshoff, A. F. Ber. Dtsch. Chem. Ges. 1898, 31, 3261-3266 10.1002/cber.189803103124
62. Singer, G. M.; Lijinsky, W.; Rainey, W. T. Org. Mass Spectrom. 1975, 10, 473-479 10.1002/oms.1210100610
63. Wedekind, E. Ber. Dtsch. Chem. Ges. 1909, 42, 3939-3941 10.1002/cber.190904203150
64. Aubineau, T.; Cossy, J. Chem. Commun. 2013, 49, 3303-3305 10.1039/c3cc40529j
65. Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266-1274 10.1002/hlca.19930760313
66. Liu, Y.; Huang, Y.; Song, H.; Liu, Y.; Wang, Q. Chem.-Eur. J. 2015, 21, 5337-5340 10.1002/chem.201406617
67. Cui, X.; Shi, F.; Tse, M. K.; Gördes, D.; Thurow, K.; Beller, M.; Deng, Y. Adv. Synth. Catal. 2009, 351, 2949-2958 10.1002/adsc.200900490
68. Steinkopf, W. J. Prakt. Chem. 1927, 117, 1-82 10.1002/prac.19271170101
69. Heller, S. T.; Sarpong, R. Org. Lett. 2010, 12, 4572-4575 10.1021/ol1018882
70. Kirmse, W.; Horner, L. Chem. Ber. 1956, 89, 1674-1680 10.1002/cber.19560890714
71. Peeters, A.; Ameloot, R.; de Vos, D. E. Green Chem. 2013, 15, 1550-1557 10.1039/c3gc40568k
72. Chen, J.; Dang, L.; Li, Q.; Ye, Y.; Fu, S.; Zeng, W. Synlett 2012, 2012, 595-600 10.1055/s-0031-1290332
73. Varela-Fernández, A.; Varela, J. A.; Saá, C. Synthesis 2012, 44, 3285-3295 10.1055/s-0032-1316539
74. Lueddens, H.; Lang, H.-J.; Korpi, E. R. Eur. J. Pharmacol. 1998, 344, 269-277 10.1016/S0014-2999(97)01577-X
75. Kawasaki, K.; Sakakibara, K. Bull. Chem. Soc. Jpn. 2007, 80, 358-364 10.1246/bcsj.80.358
76. Kurzer, F. J. Chem. Soc. 1951, 0, 1258-1262 10.1039/JR9510001258
77. Xing, M.-L.; Lu, X.-W.; Miao, C.-B.; Li, J.-X.; Sun, X.-Q.; Yang, H.-T. J. Org. Chem. 2014, 79, 11774-11779 10.1021/jo5022772
78. Goldfarb, D. S. U.S. Patent Appl. 20090163545, July 9, 2009.
79. Besenyei, G.; Németh, S.; Simándi, L. I. Tetrahedron Lett. 1991, 32, 5833-5836 10.1016/S0040-4039(00)93568-8
80. Luckhurst, C. A.; Millichip, I.; Parker, B.; Reuberson, J.; Furber, M. Tetrahedron Lett. 2007, 48, 8878-8882 10.1016/j.tetlet.2007.10.046
81. Salim, E. F.; Hilty, W. W. J. Pharm. Sci. 1967, 56, 385-386 10.1002/jps.2600560316
82. Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316-3318 10.1021/ja710206u
83. Stephens, J. U.S. Patent Appl. 3,799,760, March 26, 1974.
84. Kim, S.; Chung, Y. K. Org. Lett. 2014, 16, 4352-4355 10.1021/ol5015224
85. Fishbein, L. J. Chromatogr. A 1967, 30, 245-249 10.1016/S0021-9673(00)84147-3
86. Yin, Y.; Ma, W.; Chai, Z.; Zhao, G. J. Org. Chem. 2007, 72, 5731-5736 10.1021/jo070681h
87. Ono, K.; Fugami, K.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1994, 35, 4133-4136 10.1016/S0040-4039(00)73132-7
88. Ruschig, H.; Korger, G.; Aumuller, W.; Wagner, H.; Weyer, R.; Bander, A.; Scholz, J. Arzneim.-Forsch. 1958, 8, 448-454
89. C. F. Boehringer & Soehne GmbH Neth. Appl. 6603399, 1966.