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Synthesis 2015; 47(09): 1309-1316
DOI: 10.1055/s-0034-1380401
DOI: 10.1055/s-0034-1380401
paper
Palladium-Catalyzed ortho-Acylation of 2-Aryl-1,2,3-triazoles with Toluene Derivatives
Further Information
Publication History
Received: 01 December 2014
Accepted after revision: 23 January 2015
Publication Date:
27 February 2015 (online)

Abstract
A palladium-catalyzed ortho-acylation of 2-aryl-1,2,3-triazoles was developed in which low-toxicity, stable, commercially available toluene derivatives were used as acyl sources. A wide variety of aryl ketones containing 1,2,3-triazoles were obtained in moderate to excellent yields. A plausible mechanism is proposed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380401.
- Supporting Information
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References
- 1a Zhao D, You J, Hu C. Chem. Eur. J. 2011; 17: 5466
- 1b Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
- 1c Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
- 1d McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
- 1e Muller P, Fruit C. Chem. Rev. 2003; 103: 2905
- 1f Lewis JC, Bergman RG, Ellman JA. Acc. Chem. Res. 2008; 41: 1013
- 1g Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
- 1h Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318
- 1i Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
- 1j Pan C, Jia X, Cheng J. Synthesis 2012; 44: 677
- 2a Zhang Y.-H, Shi B.-F, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 6097
- 2b Zhang Y.-H, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 14654
- 2c Wang X, Mei T.-S, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 7520
- 2d Ball ND, Sanford MS. J. Am. Chem. Soc. 2009; 131: 3796
- 2e Zhao X, Dimitrijević E, Dong VM. J. Am. Chem. Soc. 2009; 131: 3466
- 2f Mei T.-S, Giri R, Maugel N, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 5215
- 2g Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
- 2h Giri R, Chen X, Yu J.-Q. Angew. Chem. Int. Ed. 2005; 44: 2112
- 2i Wang X.-C, Hu Y, Bonacorsi S, Hong Y, Burrell R, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 10326
- 3a Li W, Sun P. J. Org. Chem. 2012; 77: 8362
- 3b Du B, Jiang X, Sun P. J. Org. Chem. 2013; 78: 2786
- 3c Li W, Xu Z, Sun P, Jiang X, Fang M. Org. Lett. 2011; 13: 1286
- 4a Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
- 4b Zhang Q, Yang F, Wu Y. Chem. Commun. 2013; 49: 6837
- 4c Xu Z, Xiang B, Sun P. RSC Adv. 2013; 3: 1679
- 4d Li M, Ge H. Org. Lett. 2010; 12: 3464
- 5a Park J, Kim M, Sharma S, Park E, Kim A, Lee SH, Kwak JH, Jung YH, Kim IS. Chem. Commun. 2013; 49: 1654
- 5b Wu Y, Choy PY, Mao F, Kwong FY. Chem. Commun. 2013; 49: 689
- 5c Wang H, Guo L.-N, Duan X.-H. Org. Lett. 2012; 14: 4358
- 5d Wu Y, Li B, Mao F, Li X, Kwong FY. Org. Lett. 2011; 13: 3258
- 5e Yin Z, Sun P. J. Org. Chem. 2012; 77: 11339
- 5f Fang P, Li M, Ge H. J. Am. Chem. Soc. 2010; 132: 11898
- 5g Li C, Wang L, Li P, Zhou W. Chem. Eur. J. 2011; 17: 10208
- 5h Park J, Kim A, Sharma S, Kim M, Park E, Jeon Y, Lee Y, Kwak JH, Jung YH, Kim IS. Org. Biomol. Chem. 2013; 11: 2766
- 6a Tang H, Qian C, Lin D, Jiang H, Zeng W. Adv. Synth. Catal. 2014; 356: 519
- 6b Xiong F, Qian C, Lin D, Zeng W, Lu X. Org. Lett. 2013; 15: 5444
- 7 Miao J, Ge H. Org. Lett. 2013; 15: 2930
- 8 Yang Z, Chen X, Liu J, Gui Q, Xie K, Li M, Tan Z. Chem. Commun. 2013; 49: 1560
- 9a Han S, Sharma S, Park J, Kim M, Shin Y, Mishra NK, Bae JJ, Kwak JH, Jung YH, Kim IS. J. Org. Chem. 2014; 79: 275
- 9b Zhang Q, Yang F, Wu Y. Chem. Commun. 2013; 49: 6837
- 10a Guin S, Rout SK, Banerjee A, Nandi S, Patel BK. Org. Lett. 2012; 14: 5294
- 10b Weng JQ, Yu ZQ, Liu XH, Zhang GF. Tetrahedron Lett. 2013; 54: 1205
- 11 Yin ZW, Sun PP. J. Org. Chem. 2012; 77: 11339
- 12a Song H, Chen D, Pi C, Cui X, Wu Y. J. Org. Chem. 2014; 79: 2955
- 12b Xiong F, Qian C, Lin D, Zeng W, Lu X. Org. Lett. 2013; 15: 5444
- 13 Wu Y, Feng LJ, Lu X, Kwong FY, Luo H.-B. Chem. Commun. 2014; 50: 15352
- 14 Shi W, Shi ZJ. Chin. J. Chem. 2014; 32: 974
- 15a Cox CD, Breslin MJ, Whitman DB, Schreier JD, McGaughey GB, Bogusky MJ, Roecker AJ, Mercer SP, Bednar RA, Lemaire W, Bruno JG, Reiss DR, Meacham C, Murphy KL, Garson SL, Doran SM, Prueksaritanont T, Anderson WB, Tang C, Roller S, Cabalu TD, Cui D, Hartman GD, Yong SD, Kolban KS, Winrow CJ, Renger JJ, Coleman PJ. J. Med. Chem. 2010; 53: 5320
- 15b Baxter CA, Cleator E, Brands KM. J, Edwards JS, Reamer RA, Sheen FJ, Stewart GW, Strotman NA, Wallace DJ. Org. Process Res. Dev. 2011; 15: 367
- 15c Jia ZJ, Venkataramani C, Huang W, Mehrotra M, Song Y, Xu Q, Bauer SM, Pandey A. WO 2009136995, 2009
- 15d Ueda S, Su M, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 8944
- 15e He T, Wang M, Li P, Wang L. Chin. J. Chem. 2012; 30: 979
- 16a Ackermann L, Vicente R, Althammer A. Org. Lett. 2008; 10: 2299
- 16b Ackermann L, Born R, Althammer A. ChemSusChem 2009; 2: 546
- 17a Ye X, He Z, Ahmed T, Weise K, Akhmedov NG, Petersen JL, Shi X. Chem. Sci. 2013; 4: 3712
- 17b Ye X, Shi X. Org. Lett. 2014; 16: 4448
- 18a Shi S, Kuang C. J. Org. Chem. 2014; 79: 6105
- 18b Wang Z, Kuang C. Adv. Synth. Catal. 2014; 356: 1549
- 18c Wang Z, Tian Q, Yu X, Kuang C. Adv. Synth. Catal. 2014; 356: 961
- 19 Xiong F, Qian C, Lin DE, Zeng W, Lu XX. Org. Lett. 2013; 15: 5444
- 20 Wang G.-W, Yuan T.-T. J. Org. Chem. 2010; 75: 476