Direct Copper-Catalyzed C-3 Arylation of Diphenylphosphine Oxide Indoles

Abstract

We have developed a simple and effective method for the C-3 arylation of phosphorus-containing indole compounds in the presence of CuI under mild conditions. This reaction provides a reliable method for the modification of ligands.

Key words

transition-metal catalysis - organophosphorus compounds - arylation - indoles

Publication History

Received: 09 August 2021

Accepted after revision: 03 September 2021

Accepted Manuscript online:
03 September 2021

Article published online:
14 October 2021

• References

• 1a van Leeuwen PW. N. M, Kamer PC. J, Claver C, Pàmies O, Diéguez M. Chem. Rev. 2011; 111: 2077
• 1b Wang D, Weinstein AB, White PB, Stahl SS. Chem. Rev. 2018; 118: 2636
• 1c van Leeuwen PW. N. M, Kamer PC. J, Reek JN. H, Dierkes P. Chem. Rev. 2000; 100: 2741

For a review, see:
• 2a Bialy L, Waldmann H. Angew. Chem. Int. Ed. 2005; 44: 3814

For recent examples, see:
• 2b Dang Q, Liu Y, Cashion DK, Kasibhatla SR, Jiang T, Taplin F, Jacintho JD, Li H, Sun Z, Fan Y, DaRe J, Tian F, Li W, Gibson T, Lemus R, va Poelje PD, Potter SC, Erion MD. J. Med. Chem. 2011; 54: 153
• 2c Alexandre F.-R, Amador A, Bot S, Caillet C, Convard T, Jakubik J, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Roland A, Seifer M, Standring D, Storer R, Dousson CB. J. Med. Chem. 2011; 54: 392
• 2d Chen X, Kopecky DJ, Mihalic J, Jeffries S, Min X, Heath J, Deignan J, Lai S, Fu Z, Guimaraes C, Shen S, Li S, Johnstone S, Thibault S, Xu H, Cardoz M, Shen W, Walker N, Kayser F, Wang Z. J. Med. Chem. 2012; 55: 3837
• 2e Kuhn B, Hilpert H, Benz J, Binggeli A, Grether U, Humm R, Marki HP, Meyer M, Mohr P. Bioorg. Med. Chem. Lett. 2006; 16: 4016
• 3a Cho YJ, Lee JY. Chem. Eur. J. 2011; 17: 11415
• 3b Montchamp J.-L. Acc. Chem. Res. 2014; 47: 77
• 4a So CM, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2008; 47: 8059
• 4b So CM, Zhou Z, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2008; 47: 6402
• 4c So CM, Lau CP, Chan AS. C, Kwong FY. J. Org. Chem. 2008; 73: 7731
• 4d Jia T, Bellomo A, Baina KE, Dreher SD, Walsh PJ. J. Am. Chem. Soc. 2013; 135: 3740
• 4e Lee HW, Lam FL, So CM, Lau CP, Chan AS. C, Kwong FY. Angew. Chem. Int. Ed. 2009; 48: 7436
• 4f Xu M.-M, Kou L.-Y, Bao X.-G, Xu X.-P, Ji S.-J. Chin. Chem. Lett. 2021; 32: 1915
• 5 Wassenaar J, Kuil M, Reek JN. H. Adv. Synth. Catal. 2008; 350: 1610
• 6 So CM, Lau CP, Kwong FY. Org. Lett. 2007; 9: 2795

Pd-catalyzed arylations:
• 7a Deprez NR, Kalyani D, Krause A, Sanford MS. J. Am. Chem. Soc. 2006; 128: 4972
• 7b Deprez NR, Sanford MS. Inorg. Chem. 2007; 46: 1924
• 7c Deprez NR, Sanford MS. J. Am. Chem. Soc. 2009; 131: 11234
• 7d Xiao B, Fu Y, Xu J, Gong T.-J, Dai J.-J, Yi J, Liu L. J. Am. Chem. Soc. 2010; 132: 468
• 7e Pramanick PK, Zhou Z, Hou Z, Ao Y, Yao B. Chin. Chem. Lett. 2020; 31: 1327

Cu-catalyzed arylations:
• 8a Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
• 8b Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
• 8c Zhu S, MacMillan DW. C. J. Am. Chem. Soc. 2012; 134: 10815
• 8d Phipps RJ, McMurray L, Ritter S, Duong HA, Gaunt MJ. J. Am. Chem. Soc. 2012; 134: 10773
• 8e Suero MG, Bayle ED, Collins BS. L, Gaunt MJ. J. Am. Chem. Soc. 2013; 135: 5332
• 8f Kieffer ME, Chuang KV, Reisman SE. J. Am. Chem. Soc. 2013; 135: 5557
• 8g Wang Y, Chen C, Peng J, Li M. Angew. Chem. Int. Ed. 2013; 52: 5323
• 8h Collins BS. L, Suero MG, Gaunt MJ. Angew. Chem. Int. Ed. 2013; 52: 5799
• 8i Fañanás-Mastral M, Feringa BL. J. Am. Chem. Soc. 2014; 136: 9894
• 8j Wanle S, Fan L, Tang B, Hao E, Jiao L. Chin. Chem. Lett. 2019; 30: 1825
• 9a Yang Y.-Q, Li R.-R, Zhao Y, Zhao D.-B, Shi Z.-Z. J. Am. Chem. Soc. 2016; 138: 8734
• 9b Hickman AJ, Sanford MS. Nature 2012; 484: 177
• 9c Casitas A, Ribas X. Chem. Sci. 2013; 4: 2301
• 9d Wen J, Shi Z. Acc. Chem. Res. 2021; 54: 1723