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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 12
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Synthetic Communications Reviews

Pd-catalyzed regioselective C-H chlorination of disubstituted 1,2,3-triazoles

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Pages 1403-1412 | Received 21 Jan 2018, Published online: 23 May 2018

References

  • (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320–2722; (b) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945–2963; (c) Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem. Int. Ed. 2012, 51, 5062–5085; (d) Khanizeman, R. N.; Barde, E.; Bates, R. W.; Guerinot, A.; Cossy, J. Org. Lett. 2017, 19, 5046–5049.
  • (a) Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729–6731; (b) Skhiri, A.; Ben Salem, R.; Soule, J. F.; Doucet, H. ChemCatChem 2017, 9, 2895–2913; (c) Price, G. A.; Hassan, A.; Chandrasoma, N.; Bogdan, A. R.; Djuric, S. W.; Organ, M. G. Angew. Chem. Int. Ed. 2017, 56, 13347–13350.
  • (a) Miyaura, N.; Suzuki, A. J. C. S. Chem. Comm. 1979, 866–867; (b) Han, F. Chem. Soc. Rev. 2013, 42, 5270–5298; (c) Brambilla, M.; Tredwell, M. Angew. Chem. Int. Ed. 2017, 56, 11981–11985.
  • Vyas, P. V.; Bhatt, A. K.; Ramachandraiah, G.; Bedekar, A. V. Tetrahedron Lett. 2003, 44, 4085–4088.
  • Iskra, J.; Stavber, S.; Zupan, M. Synthesis 2004, 11, 1869–1873.
  • Prakash, G. K. S.; Mathew, T.; Hoole, D.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 2004, 126, 15770–15776.
  • Stowers, K. J.; Sanford, M. S. Org. Lett. 2009, 11, 4584–4587.
  • Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Tetrahedron 2006, 62, 11483–11498.
  • Chen, X.; Hao, X. S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790–6791.
  • (a)Chu, L.; Xiao, K.-J.; Yu, J.-Q. Science 2014, 346, 451–455; (b) Chu, L.; Wang, X.-C.; Moore, C. E.; Rheingold, A. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344–16347; (c) Wang, X.-C.; Hu, Y.; Bonacorsi, S.; Hong, Y.; Burrell, R.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 10326–10329; (d) Chu, L.; Shang, M.; Tanaka, K.; Chen, Q.; Pissarnitski, N.; Streckfuss, E.; Yu, J.-Q. ACS Cent. Sci. 2015, 1, 394–399.
  • Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523–2526.
  • Wan, X. B.; Ma, Z. X.; Li, B. J.; Zhang, K. Y.; Cao, S. K.; Zhang, S. W.; Shi, Z. J. J. Am. Chem. Soc. 2006, 128, 7416–7417.
  • (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, B. K. Angew. Chem. Int. Ed. 2002, 41, 2596–2599; (b) Bai, H.; Cai, Z.; Wang, S.; Ji, S. Org. Lett. 2015, 17, 2898–2901; (c) Deraedt, C.; Pinaud, N.; Astruc, D. J. Am. Chem. Soc. 2014, 136, 12092–12098; (d) Wang, Y.; Xie, Y.; Qu, H.; Wang, H.; Pan, Y.; Huang, F. J. Org. Chem. 2014, 79, 4463–4469; (e) Cheng, G.; Zeng, X.; Shen, J.; Wang, X.; Cui, X. Angew. Chem. Int. Ed. 2013, 52, 13265–13268; (f) Johansson, J. R.; Lincoln, P.; Norden, B.; Kann, N. J. Org. Chem. 2011, 76, 2355–2359; (g) Jiang, Y.; Han, C.; Liang, X.; Yang, P.; Wang, H. Youji Huaxue 2013, 33, 1884–1890; (h) Jiang, Y.; Kuang, C. Huaxue Jinzhan 2012, 24, 1983–1994; (i) Jiang, Y.; Kuang, C. Mini-Rev. Med. Chem. 2013, 13, 713–719.
  • (a) Sirivolu, V. R.; Vernekar, S. K. V.; Ilina, T.; Myshakina, N. S.; Parniak, M. A.; Wang, Z. J. Med. Chem. 2013, 56, 8765–8780; (b) Ferreira da Costa, J.; Garcia-Mera, X.; Caamano, O.; Brea, J. M.; Loza, M. I. Eur. J. Med. Chem. 2015, 98, 212–220; (c) Kuntala, N.; Telu, J. R.; Banothu, V. S.; Nallapati, B.; Anireddy, J. S.; Pal, S. MedChemComm 2015, 6, 1612–1619; (d) Gonzaga, D. T. G.; Da Rocha, D. R.; Da Silva, F. C.; Ferreira, V. F. Curr. Top. Med. Chem. 2013, 13, 2850–2865; (e) Rogers, S. A.; Melander, C. Angew. Chem. Int. Ed. 2008, 47, 5229–5231.
  • (a) He, C.; Shreeve, J. M. Angew. Chem. Int. Ed. 2015, 54, 6260–6264; (b) Padalkar, V. S.; Lanke, S. K.; Chemate, S. B.; Sekar, N. J Fluoresc. 2015, 25, 985–996; (c) Qin, J.; Zhang, S.; Du, D.; Shen, P.; Bao, S.; Lan, Y.; Su, Z. Chem. Eur. J. 2014, 20, 5625–2630; (d) Jeong, Y.; Ryu, J. J. Org. Chem. 2010, 75, 4183–4191; (e) Bolje, A.; Kosmrlj, J. Org. Lett. 2013, 15, 5084–5087; (f) Krikorian, M.; Liu, S.; Swager, T. M. J. Am. Chem. Soc. 2014, 136, 2952–2955; (g) Beltran, E. J.; Serrano, L.; Sierra, T.; Gimenez, R. J. Mater. Chem. 2012, 22, 7797–7805.
  • (a) Wang, D.; Etienne, L.; Echeverria, M.; Moya, S.; Astruc, D. Chem. Eur. J. 2014, 20, 4047–4054; (b) Ozkal, E.; Llanes, P.; Bravo, F.; Ferrali, A.; Pericas, M. A. Adv. Synth. Catal. 2014, 356, 857–869. (c) Shen, C.; Shen, H.; Yang, M.; Xia, C.; Zhang, P. Green Chem. 2015, 17, 225–230.
  • (a) Tian, Q.; Chen, X.; Liu, W.; Wang, Z.; Shi, S.; Kuang, C. Org. Biomol. Chem. 2013, 11, 7830–7833; (b) Shi, S.; Liu, W.; He, P.; Kuang, C. Org. Biomol. Chem. 2014, 12, 3576–3580; (c) Shi, S.; Kuang, C. J. Org. Chem. 2014, 79, 6105–6112; (d) Wang, Z.; Tian, Q.; Yu, X.; Kuang, C. Adv. Synth. Catal. 2014, 356, 961–966; (e) Wang, Z.; Kuang, C. Adv. Synth. Catal. 2014, 356, 1549–1554; (f) Liu, W.; Li, Y.; Xu, B.; Kuang, C. Org. Lett. 2013, 15, 2342–2345; (g) Yu, X.; Huang, Z.; Liu, W.; Shi, S.; Kuang, C. Org. Biomol. Chem. 2015, 13, 4459–4465; (h) He, P.; Tian, Q.; Kuang, C. Org. Biomol. Chem. 2015, 13, 7146–7148.
  • (a) Ackermann, L.; Vicente, R.; Born, R. Adv. Synth. Catal. 2008, 350, 741–748; (b) Chuprakov, S.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Org. Lett. 2007, 9, 2333–2335; (c) Ackermann, L.; Althammer, A.; Fenner, S. Angew. Chem. Int. Ed. 2009, 48, 201–204; (d) Ackermann, L.; Potukuchi, H. Org. Biomol. Chem. 2010, 8, 4503–4513; (e) Ackermann, L.; Jeyachandran, R.; Potukuchi, H.; Novak, P.; Buttner, L. Org. Lett. 2010, 12, 2056–2059; (f) Ackermann, L.; Potukuchi, H.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081–3084; (g) Jeyachandran, R.; Potukuchi, H.; Ackermann, L. J. Org. Chem. 2012, 8, 1771–1777.
  • (a) Zhao, S.; Yu, R.; Chen, W.; Liu, M.; Wu, H. Org. Lett. 2015, 17, 2828–2831; (b) Li, X. G.; Liu, K.; Zou, G.; Liu, P. N. Eur. J. Org. Chem. 2014, 2014, 7878–7888; (c) Ackermann, L.; Born, R.; Vicente, R. ChemSusChem 2009, 2, 546–549; (d) Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 10, 2299–2302; (e) Tirler, C.; Ackermann, L. Tetrahedron 2015, 71, 4543–4551.
  • (a) Zhao, F.; Liu, Y.; Yang, S.; Xie, K.; Jiang, Y. Org. Chem. Front. 2017, 4, 1112–1115; (b) Zhao, F.; Chen, Z.; Ma, X.; Huang, S.; Jiang, Y. Tetrahedron Lett. 2017, 58, 614–617; (c) Zhao, F.; Chen, Z.; Liu, Y.; Xie, K.; Jiang, Y. Eur. J. Org. Chem. 2016, 2016, 5971–5979; (d) Zhao, F.; Tian, W.; Luo, F.; Cheng, H.; Jiang Y.; Chen, Z. Synthetic. Commun. 2016, 46, 1678–1686; (e) Zhao, F.; Chen, Z.; Huang, S.; Jiang, Y. Synthesis 2016, 48, 2105–2111; (f) Zhao, F.; Chen, Z.; Xie, K.; Yang, R.; Jiang, Y. Chin. Chem. Lett. 2016, 27, 109–113.
  • Mindt, T.; Struthers, H.; Brans, L.; Anguelov, T.; Schweinsberg, C.; Maes, V.; Tourwe, D.; Schibli, R. J. Am. Chem. Soc. 2006, 128, 15096–15097.

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