An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

doi:10.1007/s40242-018-7305-0

Chemical Research in Chinese Universities ›› 2018, Vol. 34 ›› Issue (2): 191-196.doi: 10.1007/s40242-018-7305-0

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An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

JING Li¹, YU Xinling¹, GUAN Mei², WU Xiaohua¹, WANG Qiantao¹, WU Yong¹

1. Key Laboratory of Drug-targeting of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China;
2. West China Hospital, Sichuan University, Chengdu 610041, P. R. China

Received:2017-09-13 Revised:2017-11-17 Online:2018-04-01 Published:2017-12-18
Contact: WANG Qiantao,E-mail:qwang@scu.edu.cn;WU Yong,E-mail:wyong@scu.edu.cn E-mail:qwang@scu.edu.cn;wyong@scu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.81373259, 81573286).

Abstract

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 reaction time.

Key words: N-Fluorobenzenesulfonimide, Sulfonylation, Sulfonamide, Sulfonic ester

JING Li, YU Xinling, GUAN Mei, WU Xiaohua, WANG Qiantao, WU Yong. An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions[J]. Chemical Research in Chinese Universities, 2018, 34(2): 191-196.

References

[1] Ezabadi I. R., Camoutsis C., Zoumpoulakis P., Geronikaki A., Sokovic M., Glamocilija J., Ciric A., Bioorg. Med. Chem., 2008, 16, 1150
[2] Chohan Z. H., Youssoufi M. H., Jarrahpour A., Ben H. T., Eur J. Med. Chem., 2010, 45, 1189
[3] Chohan Z. H., Rauf A., Naseer M. M., Somra M. A., Supuran C. T., J. Enzyme Inhib. Med.Chem., 2006, 21, 173
[4] Swain S. S., Paidesetty S. K., Padhy R. N., Biomed. Pharmacother., 2017, 88, 181
[5] Tommasino J. B., Renaud F. N. R., Luneau D., Pilet G., Polyhedron, 2011, 30, 1663
[6] 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
[7] 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
[8] Kumar M., Ramasamy K., Mani V., Mishra R. K., Majeed A. B. A., Clercq E. D., Narasimhan B., Arab. J. Chem., 2014, 7, 396
[9] Keche A. P., Hatnapure G. D., Tale R. H., Rodge A. H., Kamble V. M., Bioorg. Med. Chem. Lett., 2012, 22, 6611
[10] Bano S., Javed K., Ahmad S., Rathish I. G., Singh S., Alam M. S., Eur. J. Med. Chem., 2011, 46, 5763
[11] Farag A. A., Abd-Alrahman S. N., Ahmed G. F., Ammar R. M., Ammar Y. A., Abbas S. Y., Arch. Pharm. Chem. Life Sci., 2012, 345, 703
[12] Siddiqui N., Arshad M. F., Khan S. A., Ahsan W., J. Enzyme Inhib. Med. Chem., 2010, 25, 485
[13] 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
[14] Selvam P., Chandramohan M., De Clercq E., Witvrouw M., Pannecouque C., Eur. J. Pharm. Sci., 2001, 14, 313
[15] 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
[16] Meshram G. A., Patil V. D., Tetrahedron Lett., 2009, 50, 1117
[17] Katritzky A. R., Zhang G. F., Wu J., Synthetic Commun., 1994, 24, 205
[18] Wilden J. D., Geldeard L., Lee C. C., Judd D. B., Caddick S., Chem. Commun., 2007, 10, 1074
[19] Palakurthy N. B., Mandal B., Tetrahedron Lett., 2011, 52, 7132
[20] Caddick S., Wilden J. D., Bush H. D., Wadman S. N., Judd D. B., Org. Lett., 2002, 4, 2549
[21] Yin J. J., Buchwald S. L., Org. Lett., 2000, 2, 1101
[22] Baffoe J., Hoe M. Y., Toure B. B., Org. Lett., 2010, 12, 1532
[23] Ji J., Liu Z. Y., Liu P., Sun P. P., Org. Biomol. Chem., 2016, 14, 7018
[24] Zhu H. B., Shen Y. J., Deng Q. Y., Tu T., Chem. Commun., 2015, 51, 16573
[25] Yang K., Ke M. L., Lin Y. G., Song Q. L., Green Chem., 2015, 17, 1395
[26] Yotphan S., Sumunnee L., Beukeaw D., Buathongjan C., Reutrakul V., Org. Biomol. Chem., 2016, 14, 590
[27] Parumala S. K. R., Peddinti R. K., Tetrahedron Lett., 2016, 57, 1232
[28] Moon S. Y., Nam J., Rathwell K., Kim W. S., Org. Lett., 2014, 16, 338
[29] Halperin S. D., Kwon D., Holmes M., Regalado E. L., Campeau L. C, DiRocco D. A., Britton R., Org. Lett., 2015, 17, 5200
[30] Yang K., Ke M. L., Lin Y. G., Song Q. L., Green Chem., 2015, 17, 1395
[31] Eroglu. F., Reaction Kinetics and Catalysis Letters, 2009, 98, 365
[32] Thoi I., Le V., Khao-Cuu Nien-San Khao-Hoc Dai-Hoc Duong., 1962, 73
[33] Choi J. H., J. Org. Chem., 2002, 67, 1277
[34] Hoyle J., Eds.:Patai S., Rappoport Z., The Chemistry of Sulphonic Acids, Esters, and Their Derivatives; John Wiley and Sons, New York, 1991
[35] Marquez V. E., Sharma R., Wang S., Lewin N. E., Blumberg P. M., Kim I., Lee J., Bioorg. Med. Chem. Lett., 1998, 8, 1757

An Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with N-Fluorobenzenesulfonimide Under Mild Conditions

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