Pd-NHC-Catalyzed Direct Arylation of 1,4-Disubstituted 1,2,3-Triazoles with Aryl Halides
Tao He
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
Search for more papers by this authorMin Wang
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
Search for more papers by this authorPinhua Li
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
Search for more papers by this authorCorresponding Author
Lei Wang
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China, Tel.: 0086-0561-3802069; Fax: 0086-561-03090518Search for more papers by this authorTao He
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
Search for more papers by this authorMin Wang
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
Search for more papers by this authorPinhua Li
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
Search for more papers by this authorCorresponding Author
Lei Wang
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, China, Tel.: 0086-0561-3802069; Fax: 0086-561-03090518Search for more papers by this authorAbstract
A highly efficient method for the synthesis of unsymmetrical multi-substituted 1,2,3-triazoles via a direct Pd-NHC system catalyzed C(5)-arylation of 1,4-disubstituted triazoles, which are readily accessible via "click" chemistry has been developed. It is important to note that CH bond functionalizations of 1,2,3-triazoles with a variety of differently substituted aryl iodides and bromides as electrophiles can be conveniently achieved through this catalytic system at significantly milder reaction temperatures of 100°C under air.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
Filename | Description |
---|---|
cjoc_201100275_sm_suppl.pdf313.4 KB | suppl |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1a
Modern Arylation Methods, Ed.: L. Ackermann, Wiley-VCH, Weinheim, Germany, 2009.
10.1002/9783527627325 Google Scholar
- 1b Handbook of C-H Transformations, Ed.: G. Dyker, Wiley-VCH, Weinheim, Germany, 2005.
- 2Recent reviews:
- 2a Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q.. Angew. Chem., Int. Ed., 2009, 48, 5094.
- 2b Kakiuchi, F.; Kochi, T.. Synthesis, 2008, 3013.
- 2c Li, B.-J.; Yang, S.-D.; Shi, Z.-J.. Synlett, 2008, 949.
- 2d Lewis, J. C.; Bergman, R. G.; Ellman, J. A.. Acc. Chem. Res., 2008, 41, 1013.
- 2e Satoh, T.; Miura, M.. Chem. Lett., 2007, 36, 200.
- 2f Alberico, D.; Scott, M. E.; Lautens, M.. Chem. Rev., 2007, 107, 174.
- 2g Seregin, I. V.; Gevorgyan, V.. Chem. Soc. Rev., 2007, 36, 1173.
- 2h Pascual, S.; de Mendoza, P.; Echavarren, A. M.. Org. Biomol. Chem., 2007, 5, 2727.
- 2i Campeau, L.-C.; Stuart, D. R.; Fagnou, K.. Aldrich Acta, 2007, 40, 35.
- 2j Ackermann, L.. Synlett, 2007, 507.
- 2k Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q. N.; Lazareva, A.. Synlett, 2006, 3382.
- 3For recent reviews, see:
- 3a Ackermann, L.. Top. Organomet. Chem., 2007, 24, 35.
- 3b Satoh, T.; Miura, M.. Top. Organomet. Chem., 2007, 24, 61.
- 3c Bergman, R. G.. Nature, 2007, 446, 391.
- 3d Yu, J.-Q.; Giri, R.; Chen, X.. Org. Biomol. Chem., 2006, 4, 4041.
- 4a Fan, W.-Q.; Katritzky, A. R., In Comprehensive Heterocyclic Chemistry II, Vol. 4, Eds.: A. R. Katritzky; C. W. Rees; E. F. V. Scriven, Elsevier, Oxford, UK, 1996, pp 1-126.
- 4b Whiting, M.; Muldoon, J.; Lin, Y.-C.; Silverman, S. M.; Lindstrom, W.; Olson, A. J.; Kolb, H. C.; Finn, M. G.; Sharpless, K. B.; Elder, J. H.; Fokin, V. V.. Angew. Chem., Int. Ed., 2006, 45, 1435.
- 4c Bourne, Y.; Kolb, H. C.; Radi?, Z.; Sharpless, K. B.; Taylor, P.; Marchot, P.. Proc. Natl. Acad. Sci., 2004, 101, 1449.
- 4d
Lewis, W. G.;
Green, L. G.;
Grynszpan, F.;
Radi?, Z.;
Carlier, P. R.;
Taylor, P.;
Finn, M. G.;
Sharpless, K. B..
Angew. Chem., Int. Ed.,
2002,
41,
1053.
10.1002/1521-3773(20020315)41:6<1053::AID-ANIE1053>3.0.CO;2-4 CAS PubMed Web of Science® Google Scholar
- 4e Alvarez, R.; Velazques, S.; San, F.; Aquaro, S.; De, C.; Perno, C. F.; Karlesson, A.; Balzarini, J.; Camarasa, M. J.. J. Med. Chem., 1994, 37, 4185.
- 4f Ackermann, L.; Potukuchi, H. K.. Org. Biomol. Chem., 2010, 8, 4503.
- 5For recent reviews, see:
- 5a Krivopalov, V. P.; Shkurko, O. P.. Russ. Chem. Rev., 2005, 74, 339.
- 5b Tome, A. C., In Science of Synthesis, Vol. 13, Eds.: R. Stor; T. Gilchrist, Thieme, New York, 2004, pp. 415-601.
- 6a
Rostovtsev, V. V.;
Green, L. G.;
Fokin, V. V.;
Sharpless, K. B..
Angew. Chem., Int. Ed.,
2002,
41,
2596.
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 CAS PubMed Web of Science® Google Scholar
- 6b Tornøe, C. W.; Christensen, C.; Meldal, M.. J. Org. Chem., 2002, 67, 3057.
- 7 Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G.. J. Am. Chem. Soc., 2005, 127, 15998.
- 8For example for biologically active 1,4,5-trisubstituted 1,2,3-triazoles, inhibitors of tumor necrosis factor-α(TNT-α) and antagonists for GABA receptors have been reported.
- 8a Tullis, J. S.; VanRens, J. C.; Natchus, M. G.; Clark, M. P.; De, B.; Hsieh, L. C.; Janusz, M. J.. Bioorg. Med. Chem. Lett., 2003, 13, 1665.
- 8b Alam, M. S.; Huang, J.; Ozoe, F.; Matsumura, F.; Ozoe, Y.. Bioorg. Med. Chem. Lett., 2007, 15, 5090.
- 9a Labbe, G.. Chem. Rev., 1969, 69, 345.
- 9b Wang, Z.-X.; Qin, H.-L.. Chem. Commun., 2003, 2450.
- 9c Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y.. Tetrahedron Lett., 2002, 43, 9707.
- 9d Díez-González, S.; Correa, A.; Cavallo, L.; Nolan, S. P.. Chem. Eur. J., 2006, 12, 7558.
- 9e Majireck, M.; Weinreb, S. M.. J. Org. Chem., 2006, 71, 8680 and references cited therein.
- 10 Chuprakov, S.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V.. Org. Lett., 2007, 9, 2333.
- 11 Ackermann, L.; Vicete, R.. Org. Lett., 2009, 11, 4922.
- 12 Iwasaki, M.; Yorimitsu, H.; Oshima, K.. Chem. Asian J., 2007, 2, 1430.
- 13 Ackermann, L.; Vicente, R.; Born, R.. Adv. Synth. Catal., 2008, 350, 741.
- 14 Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Viente, R.. Org. Lett., 2008, 10, 3081.
- 15 Fukuzawa, S.; Shimizu, E.; Ogata, K.. Heterocycles, 2009, 78, 645.
- 16a Herrmann, W. A.; K?cher, C.. Angew. Chem., Int. Ed., 1997, 36, 2162.
- 16b Arduengo, A.. Acc. Chem. Res., 1999, 32, 913.
- 16c Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G.. Chem. Rev., 2000, 100, 39.
- 16d
Herrmann, W. A..
Angew. Chem., Int. Ed.,
2002,
41,
1290.
10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y CAS PubMed Web of Science® Google Scholar
- 16e Liddle, S. T.; Edworthy, I. S.; Arnold, P. L.. Chem. Soc. Rev., 2007, 36, 1732.
- 16f Garrison, J. C.; Youngs, W. J.. Chem. Rev., 2005, 105, 3978.
- 16g González, S. D.; Nolan, S. P.. Synlett, 2007, 2158.
- 16h Trnka, T. M.; Grubbs, R. H.. Acc. Chem. Res., 2001, 34, 18.
- 16i Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G.. Angew. Chem., Int. Ed., 2007, 46, 2768.
- 16j
Nolan, S. P., N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, Weinheim, 2006.
10.1002/9783527609451 Google Scholar
- 16k Wang, M.; Li, P. H.; Wang, L.. Eur. J. Org. Chem., 2008, 2255.
- 17 Green, J. C.; Scur, R. G.; Arnold, P. L.; Cloke, G. N.. Chem. Commun., 1997, 1963.
- 18 Hahn, E. F.; Jahnke, M. C.. Angew. Chem., Int. Ed., 2008, 47, 3122.
- 19Review on NHCs and their applications in organic synthesis:
- 19a Diez-Gonzalez, S.; Nolan, S. P.. Coord. Chem. Rev., 2007, 251, 874.
- 19b Mata, J. A.; Poyatos, M.; Peris, E.. Coord. Chem. Rev., 2007, 251, 841.
- 19c
Gstottmayr, C. W. K.;
Bohm, V. P. W.;
Herdtweck, E.;
Grosche, M.;
Herrmann, W. A..
Angew. Chem., Int. Ed.,
2002,
41,
1363.
10.1002/1521-3773(20020415)41:8<1363::AID-ANIE1363>3.0.CO;2-G CAS PubMed Web of Science® Google Scholar
- 19d Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P.. J. Org. Chem., 1999, 64, 3804.
- 19e Yang, C.; Lee, H. M.; Nolan, S. P.. Org. Lett., 2001, 3, 1511.
- 19f Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Huack, S. I.; Hartwig, J. F.. Org. Lett., 2000, 2, 1423.
- 20 Arduengo, A. J.; Harlow, R. L.; Kline, M.. J. Am. Chem. Soc., 1991, 113, 361.
- 21 Huang, J. H.; Macdonald, S. J. F.; Harrity, J. P. A.. Chem. Commun., 2009, 436.
- 22 Huang, J. H.; Macdonald, S. J. F.; Cooper, A. W. J.; Fisher, G.; Harrity, J. P. A.. Tetrahedron Lett., 2009, 50, 5539.