Visible-Light-Induced Difluoromethylation/Cyclization of 1-Acryloyl-2-cyanoindoles by [Bis(difluoroacetoxy)iodo]benzene under Catalyst-Free Conditions

Abstract

We have developed a visible-light-induced radical cascade difluoromethylation/cyclization reaction of 1-acryloyl-2-cyanoindoles with [bis(difluoroacetoxy)iodo]benzene under catalyst-free conditions. The use of shelf-stable and easily accessible difluoromethylation reagents, combined with environmentally friendly and mild reaction conditions, makes this method an alternative strategy for the synthesis of difluoroalkylated pyrrolo[1,2-a]indolediones.

Key words

visible-light-induced - difluoromethylation - 1-acryloyl-2-cyanoindoles - [bis(difluoroacetoxy)iodo]benzene - catalyst-free

Publication History

Received: 12 February 2025

Accepted after revision: 12 March 2025

Accepted Manuscript online:
13 March 2025

Article published online:
13 May 2025

• References

• 1 Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
• 2 Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
• 3 Hagmann WK. J. Med. Chem. 2008; 51: 4359
• 4 Wang J, Sanchez-Rosello M, Acena JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
• 5 Gillis EP, Eastman KJ, Hill MD, Donnelly DJ, Meanwell NA. J. Med. Chem. 2015; 58: 8315
• 6a Erickson JA, McLoughlin JI. J. Org. Chem. 1995; 60: 1626
• 6b Meanwell NA. J. Med. Chem. 2011; 54: 2529
• 7a Vaswani RG, Day JJ, Wood JL. Org. Lett. 2009; 11: 4532
• 7b Li L, Chen Z, Zhang XW, Jia YX. Chem. Rev. 2018; 118: 3752
• 7c Lu YH, Wu C, Hou JC, Wu ZL, Zhou MH, Huang XJ, He WM. ACS Catal. 2023; 13: 13071
• 7d Chen X, Jiang J, Huang XJ, He WM. Org. Chem. Front. 2023; 10: 3898
• 8a Zhou X, Fan Z, Zhang Z, Lu P, Wang Y. Org. Lett. 2016; 18: 4706
• 8b Vallakati R, May JA. J. Am. Chem. Soc. 2012; 134: 6936
• 8c Cui Z, Du DM. J. Org. Chem. 2018; 83: 5149
• 9a Huang AX, Zhu HL, Zeng FL, Chen XL, Huang XQ, Qu LB, Yu B. Org. Lett. 2022; 24: 3014
• 9b Luo W, Huang AX, Chen Z, Yu B. New J. Chem. 2025; 49: 13
• 9c Huang AX, Fu YR, Zhu HL, Zeng FL, Chen XL, Tang S, Qu LB, Yu B. J. Org. Chem. 2022; 87: 14433
• 10 Yuan JW, Shen L, Guo N, Yin Y, Yang P, Yang L, Xiao Y, Zhang S. J. Org. Chem. 2023; 88: 16598
• 11 Qu HZ, Yuan JW, Feng ZD, Guo N, Yin YL, Yang LR, Xiao YM, Qu LB. Adv. Synth. Catal. 2024; 366: 1158
• 12 Lv WX, Yang PY, Yuan JW, Li JY, Liang MR, Liu YT, Xing DL, Yang LR. J. Org. Chem. 2024; 89: 3525
• 13 Sakamoto R, Kashiwagi H, Maruoka K. Org. Lett. 2017; 19: 5126
• 14a Wang Y, Yang Y, Wang C. Chin. J. Chem. 2019; 37: 1229
• 14b Meyer CF, Hell SM, Misale A, Trabanco AA, Gouverneur V. Angew. Chem. Int. Ed. 2019; 58: 8829
• 15a Zhao Y, Zhang Y, Liu YT, Zhu TH, Wu J. Org. Chem. Front. 2021; 8: 5948
• 15b Wang L, Zhang Y, Zhu T, Wu J. J. Org. Chem. 2022; 87: 7551
• 16a Lu K, Lei L, Wei Q, Zhou T, Jia X, Li Q, Zhao X. Tetrahedron Lett. 2021; 67: 152864
• 16b Wei Q, Lei L, Zhou T, Li A, Liu J, Zhao X, Lu K. Tetrahedron 2021; 91: 132217
• 16c Lu K, Zhou T, Jia X, Wei P, Lei L, Xi X, Liu J, Zhao X. Asian J. Org. Chem. 2021; 10: 563
• 16d Wang XX, Liu RY, Zhang SY, Zhou T, Zhao X, Lu K. Tetrahedron Lett. 2022; 96: 153761
• 16e Zhou NN, Liu RY, Zhang CM, Wang K, Feng JX, Zhao X, Lu K. Org. Lett. 2022; 24: 3576
• 17a Zhou NN, Wang K, Zhao TT, Liu RY, Rui MY, Zhao X, Feng JX, Lu K. Asian J. Org. Chem. 2022; 11: e202200386
• 17b Liu RY, Zhou NN, Zhao TT, Zhang Y, Wang K, Zhao X, Lu K. J. Org. Chem. 2023; 88: 483
• 17c Zhang Y, Liu Y, Zhang Y, Zhu Y, Zhou NN, Zhao X, Lu K. J. Org. Chem. 2024; 89: 1199
• 17d Zhu YQ, Yi FC, Zhou NN, Zhang Y, Zhang Y, Zhao X, Lu K. Org. Biomol. Chem. 2024; 22: 7024