Ruthenium-catalyzed C–H Sulfonamidation of 4-Aryl-7H-pyrrolo[2,3-d] pyrimidine with Sulfonyl Azides Under Aerobic Atmosphere

Abstract

Ruthenium-catalyzed arene ortho C−H sulfonamidation of 4-aryl-7H-pyrrolo[2,3-d]pyrimidine derivatives with sulfonyl azides under aerobic conditions is described. This transformation has the advantages of operational simplicity, good functional group compatibility, broad substrate scope, and mild conditions, affording a variety of sulfonamidated pyrrolo[2,3-d]pyrimidine derivatives in good to excellent yields. Oxygen plays a vital role in this unique reactivity.

Keywords

C–H sulfonamidation - Pyrrolo[2,3-d]pyrimidine - Sulfonyl azides - Site-selectivity - [RuCl₂(p-cymene)]₂ - Under aerobic conditions

Publikationsverlauf

Eingereicht: 19. Dezember 2025

Angenommen nach Revision: 26. Januar 2026

Accepted Manuscript online:
27. Januar 2026

Artikel online veröffentlicht:
06. Februar 2026

• References

• 1 Sk MR, Bera SS, Basuli S, Metya A, Maji MS. Asian J Org Chem 2020; 9: 1701-1717
• 2 Kumari S, Carmona AV, Tiwari AK, Trippier PC. J Med Chem 2020; 63: 12290-12358
• 3 Remko M. J Mol Struct 2010; 944: 34-42
• 4 Sosunovych B, Vashchenko BV, Andriashvili VA, Grygorenko OO. Chem Rec 2023; e202300258
• 5 Liu Z, Ebadi A, Toughani M, Mert N, Vessally E. RSC Adv 2020; 10: 37299-37313
• 6 Rao MVK, Kareem S, Vali SR, Reddy BVS. Org Biomol Chem 2023; 21: 8426-8462
• 7 Wishart DS, Feunang YD, Guo AC. et al. Nucleic Acids Res 2018; 46: D1074-D1082
• 8 Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S. J Am Chem Soc 2012; 134: 9110-9113
• 9 Shi J, Zhou B, Yang Y, Li Y. Org Biomol Chem 2012; 10: 8953-8955
• 10a Jia X, Han J. J Org Chem 2014; 79: 4180-4185
• 10b Wang H, Yu Y, Hong X, Tan Q, Xu B. J Org Chem 2014; 79: 3279-3288
• 10c Zhang C, Zhou Y, Deng Z, Chen X, Peng Y. Eur J Org Chem 2015; 1735-1744
• 10d Ma JL, Zhou XM, Chen JL. et al. Org Biomol Chem 2022; 20: 7554-7576
• 11a Yadav MR, Rit RK, Sahoo AK. Org Lett 2013; 15: 1638-1641
• 11b Bhanuchandra M, Yadav MR, Rit RK, Kurama MR, Sahoo AK. Chem Commun 2013; 49: 5225-5227
• 11c Kim J, Kim J, Chang S. Chem Eur J 2013; 19: 7328-7333
• 11d Thirunavukkarasu VS, Raghuvanshi K, Ackermann L. Org Lett 2013; 15: 3286-3289
• 11e Zhou X, Luo P, Long L, Ouyang M, Sang X, Ding Q. Tetrahedron 2014; 70: 6742-6748
• 11f Pan C, Abdukader A, Han J, Cheng Y, Zhu C. Chem Eur J 2014; 20: 3606-3609
• 11g Wang X, Zhang C, Li J. et al. RSC Adv 2016; 6: 68929-68933
• 11h Xiao X, Jia G, Liu F, Ou G, Xie Y. J Org Chem 2018; 83: 13811-13820
• 11i Bakthadoss M, Kumar PV, Kumar R, Surender M, Shadra DS. New J Chem 2019; 43: 14190-14195
• 12a Kong X, Lin L, Xu B. Adv Synth Catal 2018; 360: 2801-2805
• 12b Kong X, Xu B. Asian J Org Chem 2019; 8: 1862-1865
• 13 Hu Z, Luo S, Zhu Q. Sci China Chem 2015; 58: 1349-1353
• 14 Sun B, Yoshino T, Matsunaga S, Kanai M. Adv Synth Catal 2014; 356: 1491-1495
• 15a Lee D, Kim Y, Chang S. J Org Chem 2013; 78: 11102-11109
• 15b Shin K, Chang S. J Org Chem 2014; 79: 12197-12204
• 15c Hou W, Yang Y, Ai W. et al. Eur J Org Chem 2015; 395-400
• 15d Kim Y, Park J, Chang S. Org Lett 2016; 18: 1892-1895
• 15e Hermann GN, Becker P, Bolm C. Angew Chem Int Ed 2016; 55: 3781-3784
• 15f Chen S, Feng B, Zheng X, Yin J, Yang S, You J. Org Lett 2017; 19: 2502-2505
• 15g Lanke V, Prabhu KR. Chem Commun 2017; 53: 5117-5120
• 15h Wang L, Yang Z, Yang M, Zhang R, Kuai C, Cui X. Org Biomol Chem 2017; 15: 8302-8307
• 15i Hou H, Zhao Y, Sheng S. J Chen, Adv Synth Catal 2019; 361: 4393-4398
• 15j Xiong H, Gu Y, Zhang S. et al. Chem Commun 2020; 56: 4692-4695
• 16 Dinakaran VS, Bomma B, Srinivasan KK. Der Pharma Chem 2012; 4: 255-265
• 17a Zhou J, Mao ZT, Pan HK, Zhang XX. Org Chem Front 2020; 7: 324-328
• 17b Liu M, Mao ZT, Jiang YF, Zhang Z, Zhang XX. Tetrahedron Lett 2022; 96: 153754
• 17c Liu M, Shen CW, Tang T, Pan CH, Liu MR, Zhang XX. Org Lett 2023; 25: 2637-2641
• 18 Mao ZT, Liu M, Zhu GY, Zhou J, Zhang XX. Org Chem Front 2020; 7: 2696-2702
• 19 Jiang YF, Pan CH, Tang T, Liu MR, Zhang XX. Org Biomol Chem 2023; 21: 2748-2753
• 20 Pan CH, He C, Wang JR, Tang JY, Zhang XX. Org Biomol Chem 2024; 22: 1181-1185
• 21 Liu MR, Li N, Zhu QB. et al. Tetrahedron 2024; 155: 133912
• 22 Zhang Z, Liu MR, Liu M, Pan CH, Mao ZT, Zhang XX. J Org Chem 2024; 89: 2996-3009
• 23a Zhang Z, Shen CW, Tang JY, Wang JR, Cui XX, Zhang XX. Tetrahedron 2024; 159: 134008
• 23b Kim JY, Park SH, Ryu J. et al. J Am Chem Soc 2012; 134: 9110-9113
• 23c Shin K, Kim H, Chang S. Acc Chem Res 2015; 48: 1040-1052