Chemoselective Organoclick–Click Sequence

Published as part of the Special Section on the 26th French–Japanese Symposium on Medicinal and Fine Chemistry

Abstract

A highly chemoselective bis-triazole synthesis based on a sequence organocatalyzed click reaction/copper-catalyzed click reaction is described in this paper. A range of bis-azides react with various ketones using proline catalysis through the aryl azide moiety while the alkyl azide one remains available for a metal-catalyzed triazole synthesis.

Key words

triazoles - organocatalysis - organoclick reaction - click reaction - chemoselectivity

• References

• 1 Shenvi RA. O’Malley DP. Baran PS. Acc. Chem. Res. 2009; 42: 530
• 2 For example, see: Fors BP. Watson DA. Biscoe MR. Buchwald SL. J. Am. Chem. Soc. 2008; 130: 13552
• 3 For example, see: Qureshi Z. Kim JY. Bruun T. Lam H. Lautens M. ACS Catal. 2016; 6: 4946
• 4 For an excellent review on the concept of bio-orthogonal chemistry, see: Sletten EM. Bertozzi CR. Angew. Chem. Int. Ed. 2009; 48: 6974
• 5 Tornoe CW. Christensen C. Meldal M. J. Org. Chem. 2002; 67: 3057
• 6 Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
• 7 Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 75: 604
• 8 About the concept of click chemistry, see: Kolb HC. Finn MG. Sharpless KB.. Angew. Chem. Int. Ed. 2001; 40: 2004
• 9 For a review, see: Hein JE. Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
• 10 For a review, see: Thirumurugan P. Matosiuk D. Jozwiak K. Chem. Rev. 2013; 113: 4905
• 11 Rasmussen LK. Boren BC. Fokin VV. Org. Lett. 2007; 9: 5337
• 12 Kwok SW. Fotsing JR. Fraser RJ. Rodionov VO. Fokin VV. Org. Lett. 2010; 12: 4217
• 13 Sletten EM. Bertozzi CR. Acc. Chem. Res. 2011; 44: 666
• 14 Wittig G. Krebs A. Chem. Ber. 1961; 94: 3260

For reviews, see:
• 15a Renzi P. Bella M. Chem. Commun. 2012; 48: 6881
• 15b Ramasastry SS. V. Angew. Chem. Int. Ed. 2014; 53: 14310
• 15c John J. Thomas J. Dehaen W. Chem. Commun. 2015; 51: 10797
• 15d Jalani HB. Karagöz AC. Tsogoeva SB. Synthesis 2017; 49: 29
• 16a Ramachary DB. Ramakumar K. Narayana VV. Chem. Eur. J. 2008; 14: 9143
• 16b Danence LJ. T. Gao Y. Li M. Huang Y. Wang J. Chem. Eur. J. 2011; 17: 3584
• 16c Belkheira M. El Abed D. Pons J.-M. Bressy C. Chem. Eur. J. 2011; 17: 12917
• 17 Ramachary DB. Shashank AB. Karthik S. Angew. Chem. Int. Ed. 2014; 53: 10420
• 18 Thomas J. John J. Parekh N. Dehaen W. Angew. Chem. Int. Ed. 2014; 53: 10155
• 19 Thomas J. Jana S. John J. Liekens S. Dehaen W. Chem. Commun. 2016; 52: 2885
• 20 For a review, see: Zheng Z.-J. Wang D. Xu Z. Xu L.-W. Beilstein J. Org. Chem. 2015; 11: 2557
• 21a Aucagne V. Leigh DA. Org. Lett. 2006; 8: 4505
• 21b Fiandanese V. Bottalico D. Marchese G. Punzi A. Capuzzolo F. Tetrahedron 2009; 65: 10573
• 22a Grée D. Grée R. Tetrahedron Lett. 2010; 51: 2218
• 22b Elamari H. Meganem F. Herscovici J. Girard C. Tetrahedron Lett. 2011; 52: 658
• 22c Beal DM. Albrow VE. Burslem G. Hitchen L. Fernandes C. Lapthorn C. Roberts LR. Selby MD. Jones LH. Org. Biomol. Chem. 2012; 10: 548
• 22d Hatit MZ. C. Sadler JC. McLean LA. Whitehurst BC. Seah CP. Humphreys LD. Young RJ. Watson AJ. B. Burley GA. Org. Lett. 2016; 18: 1694
• 23 Wright K. Quinodoz P. Drouillat B. Couty F. Chem. Commun. 2017; 53: 321
• 24 Yuan Z. Huang G.-C. Clark RJ. Zhu L. Org. Lett. 2012; 14: 2590
• 25 Brotheton WS. Michaels HA. Simmons JT. Clark RJ. Dalal NS. Zhu L. Org. Lett. 2009; 14: 4954
• 26 Yoshida S. Misawa Y. Hosoya T. Eur. J. Org. Chem. 2014; 3991
• 27 Alajarin M. Bonillo B. Sanchez-Andrada P. Vidal A. Bautista D. J. Org. Chem. 2007; 72: 5863