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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
MissingFormLabel
- 1c Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
MissingFormLabel
- 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
MissingFormLabel
- 1h Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318
MissingFormLabel
- 1i Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
MissingFormLabel
- 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
MissingFormLabel
- 2b Zhang Y.-H, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 14654
MissingFormLabel
- 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
MissingFormLabel
- 3a Li W, Sun P. J. Org. Chem. 2012; 77: 8362
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 5c Wang H, Guo L.-N, Duan X.-H. Org. Lett. 2012; 14: 4358
MissingFormLabel
- 5d Wu Y, Li B, Mao F, Li X, Kwong FY. Org. Lett. 2011; 13: 3258
MissingFormLabel
- 5e Yin Z, Sun P. J. Org. Chem. 2012; 77: 11339
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 7 Miao J, Ge H. Org. Lett. 2013; 15: 2930
MissingFormLabel
- 8 Yang Z, Chen X, Liu J, Gui Q, Xie K, Li M, Tan Z. Chem. Commun. 2013; 49: 1560
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 17a Ye X, He Z, Ahmed T, Weise K, Akhmedov NG, Petersen JL, Shi X. Chem. Sci. 2013; 4: 3712
MissingFormLabel
- 17b Ye X, Shi X. Org. Lett. 2014; 16: 4448
- 18a Shi S, Kuang C. J. Org. Chem. 2014; 79: 6105
MissingFormLabel
- 18b Wang Z, Kuang C. Adv. Synth. Catal. 2014; 356: 1549
MissingFormLabel
- 18c Wang Z, Tian Q, Yu X, Kuang C. Adv. Synth. Catal. 2014; 356: 961
MissingFormLabel
- 19 Xiong F, Qian C, Lin DE, Zeng W, Lu XX. Org. Lett. 2013; 15: 5444
MissingFormLabel
- 20 Wang G.-W, Yuan T.-T. J. Org. Chem. 2010; 75: 476