Abstract
A new and convenient procedure was developed for the preparation of sulfonamides and sulfonic esters using N-fluorobenzenesulfonimide(NFSI) as a novel phenylsulfonyl group transfer reagent. In this protocol, a broad range of functional groups were tolerated to give the corresponding sulfonamides or sulfonic esters in moderate to excellent yields. The synthetic strategy for sulfonamides formation proceeded efficiently even under base-, metal- and additive-free conditions with the advantages of operational simplicity, mild reaction conditions as well as short reac-tion time.
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Ezabadi I. R., Camoutsis C., Zoumpoulakis P., Geronikaki A., So-kovic M., Glamocilija J., Ciric A., Bioorg. Med. Chem., 2008, 16, 1150
Chohan Z. H., Youssoufi M. H., Jarrahpour A., Ben H. T., Eur J. Med. Chem., 2010, 45, 1189
Chohan Z. H., Rauf A., Naseer M. M., Somra M. A., Supuran C. T., J. Enzyme Inhib. Med. Chem., 2006, 21, 173
Swain S. S., Paidesetty S. K., Padhy R. N., Biomed. Pharmacother., 2017, 88, 181
Tommasino J. B., Renaud F. N. R., Luneau D., Pilet G., Polyhedron, 2011, 30, 1663
Lu X. Y., Wang Z. C., Ren S. Z., Shen F. Q., Man R. J., Zhu H. L., Bioorg. Med. Chem. Lett., 2016, 26, 3491
Ghorab M. M., Alsaid M. S., El-Gaby M. S. A., Safwat N. A., Elaasser M. M., Soliman A. M., Eur. J. Med. Chem., 2016, 124, 299
Kumar M., Ramasamy K., Mani V., Mishra R. K., Majeed A. B. A., Clercq E. D., Narasimhan B., Arab. J. Chem., 2014, 7, 396
Keche A. P., Hatnapure G. D., Tale R. H., Rodge A. H., Kamble V. M., Bioorg. Med. Chem. Lett., 2012, 22, 6611
Bano S., Javed K., Ahmad S., Rathish I. G., Singh S., Alam M. S., Eur. J. Med. Chem., 2011, 46, 5763
Farag A. A., Abd-Alrahman S. N., Ahmed G. F., Ammar R. M., Am-mar Y. A., Abbas S. Y., Arch. Pharm. Chem. Life Sci., 2012, 345, 703
Siddiqui N., Arshad M. F., Khan S. A., Ahsan W., J. Enzyme Inhib. Med. Chem., 2010, 25, 485
Zhao X. Z., Maddali K., Smith S. J., Métifiot M., Johnson B. C., Marchand C., Hughes S. H., Pommier Y., Burke Jr T. R., Bioorg. Med. Chem. Lett., 2012, 22, 7309
Selvam P., Chandramohan M., De Clercq E., Witvrouw M., Panne-couque C., Eur. J. Pharm. Sci., 2001, 14, 313
Zhao Z., Wolkenberg S. E., Sanderson P. E., Lu M., Munshi V., Moyer G., Feng M., Carella A. V., Ecto L. T., Gabryelski L. J., Lai M. T., Prasad S. G., Yan Y., McGaughey G. B., Miller M. D., Lindsley C. W., Hartman G. D., Vacca J. P., Williams T. M., Bioorg. Med. Chem. Lett., 2008, 18, 554
Meshram G. A., Patil V. D., Tetrahedron Lett., 2009, 50, 1117
Katritzky A. R., Zhang G. F., Wu J., Synthetic Commun., 1994, 24, 205
Wilden J. D., Geldeard L., Lee C. C., Judd D. B., Caddick S., Chem. Commun., 2007, 10, 1074
Palakurthy N. B., Mandal B., Tetrahedron Lett., 2011, 52, 7132
Caddick S., Wilden J. D., Bush H. D., Wadman S. N., Judd D. B., Org. Lett., 2002, 4, 2549
Yin J. J., Buchwald S. L., Org. Lett., 2000, 2, 1101
Baffoe J., Hoe M. Y., Toure B. B., Org. Lett., 2010, 12, 1532
Ji J., Liu Z. Y., Liu P., Sun P. P., Org. Biomol. Chem., 2016, 14, 7018
Zhu H. B., Shen Y. J., Deng Q. Y., Tu T., Chem. Commun., 2015, 51, 16573
Yang K., Ke M. L., Lin Y. G., Song Q. L., Green Chem., 2015, 17, 1395
Yotphan S., Sumunnee L., Beukeaw D., Buathongjan C., Reutrakul V., Org. Biomol. Chem., 2016, 14, 590
Parumala S. K. R., Peddinti R. K., Tetrahedron Lett., 2016, 57, 1232
Moon S. Y., Nam J., Rathwell K., Kim W. S., Org. Lett., 2014, 16, 338
Halperin S. D., Kwon D., Holmes M., Regalado E. L., Campeau L. C, DiRocco D. A., Britton R., Org. Lett., 2015, 17, 5200
Yang K., Ke M. L., Lin Y. G., Song Q. L., Green Chem., 2015, 17, 1395
Eroglu. F., Reaction Kinetics and Catalysis Letters, 2009, 98, 365
Thoi I., Le V., Khao-Cuu Nien-San Khao-Hoc Dai-Hoc Duong., 1962, 73
Choi J. H., J. Org. Chem., 2002, 67, 1277
Hoyle J., Eds.: Patai S., Rappoport Z., The Chemistry of Sulphonic Acids, Esters, and Their Derivatives; John Wiley and Sons, New York, 1991
Marquez V. E., Sharma R., Wang S., Lewin N. E., Blumberg P. M., Kim I., Lee J., Bioorg. Med. Chem. Lett., 1998, 8, 1757
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Supported by the National Natural Science Foundation of China(Nos.81373259, 81573286).
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An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions
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Jing, L., Yu, X., Guan, M. et al. An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions. Chem. Res. Chin. Univ. 34, 191–196 (2018). https://doi.org/10.1007/s40242-018-7305-0
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DOI: https://doi.org/10.1007/s40242-018-7305-0