Abstract
The chapter concentrates on mechanistic aspects of thermal and metal catalysed reactions of organic azides and alkynes, particularly terminal alkynes, that result in the formation of 1,2,3-triazoles.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Biagi G, Giorgi I, Livi O, Scartoni V, Betti L, Giannaccini G, Trincavelli ML (2002) Eur J Med Chem 37:565
Danence LJT, Gao Y, Li M, Huang H, Wang J (2011) Chem Eur J 17:3584
Stazi F, Cancogni D, Turco L, Westerduin P, Bacchi S (2010) Tetrahedron Lett 51:5385
Huisgen R (1961) Proc Chem Soc 357
Husigen R (1963) Angew Chem Int Ed 2:565
Huisgen R (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry, vol 1. Wiley, New York, pp 1–176
Huisgen R, Szeimes G, Möbius L (1967) Chem Ber 100:2494
Padwa A, Pearson WH (eds) (2003) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. Wiley, Hoboken, New Jersey
Michael A (1883) J Prakt Chem 48:94
Mitchell G, Rees CW (1987) J Chem Soc Perkin Trans 1 413
Honda K, Nakanishi H, Nagawa Y, Yabe A (1984) J Chem Soc Chem Commun 450
Nagawa Y, Honda K, Nakanishi H (1987) Synthesis 905
Wittig G, Krebs A (1961) Chem Ber 94:3260
Jewett JC, Bertozzi CR (2010) Chem Soc Rev 39:1272
Debets MF, van der Doelen CWJ, Rutjes FPJT, van Delft FL (2010) ChemBioChem 11:1168
Agard NJ, Prescher JA, Bertozzi CR (2004) J Am Chem Soc 126:15046
Ning X, Temming RP, Dommerholt J, Guo J, Ania DB, Debets MF, Wolfert MA, Boons G-J, van Delft FL (2010) Angew Chem Int Ed 49:3065
Sletten EM, Nakamura H, Jewett JC, Bertozzi CR (2010) J Am Chem Soc 132:11799
Plass T, Milles S, Koehler C, Schultz C, Lemke EA (2011) Angew Chem Int Ed 50:3878
Kirmse W, Horner L (1958) Liebigs Ann Chem 614:1
Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, Chichester, p 156
Meazza G, Zanardi G (1991) J Fluorine Chem 55:199
van Berkel SS, Dirks AJ, Meeuwissen SA, Pingen DLL, Boerman OC, Laverman P, van Delft FL, Cornelissen JJLM, Rutjes FPJT (2008) ChemBioChem 9:1805
Huang J, Macdonald SJF, Harrity JPA (2009) Chem Commun 436
Englert BC, Bakbak S, Bunz UHF (2005) Macromolecules 38:5868
Jiang Y, Kuang C, Yang Q (2011) Tetrahedron 67:289
Krasinski A, Fokin VV, Sharpless KB (2004) Org Lett 6:1237
Liu D, Gao W, Dai Q, Zhang X (2005) Org Lett 7:4907
Dai Q, Gao W, Liu D, Capes LM, Zhang X (2006) J Org Chem 71:3928
Odlo K, Hentzen J, Fournier dit Chabert J, Ducki S, Gani OABS, Sylte I, Skrede M, Flørenes VA, Hansen TV (2008) Bioorg Med Chem 16:4829
Chakraborty A, Dey S, Sawoo S, Ardash NN, Sakar A (2010) Organometallics 29:6619
Heaney H, Ley SV (1973) J Chem Soc Perkin Trans 1 499
Yuan Y, Thomé I, Kim SH, Chen D, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C (2010) Adv Synth Catal 352:2892
Kwok SW, Fotsing JR, Fraser RJ, Rodionov VO, Fokin VV (2010) Org Lett 12:4217
Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G (2005) J Am Chem Soc 127:15998
Rasmussen LK, Boren BC, Fokin VV (2007) Org Lett 9:5337
Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV (2008) J Am Chem Soc 130:8923
Lipshutz BH, Sengupta S (1992) Org React 41:135
Taylor RJK (ed) (1994) Organocopper reagents. Oxford University Press, Oxford
Lipshutz BH (2002) In: Schlosser M (ed) Organometallics in synthesis, a manual. Wiley, Chichester
Krause N (ed) (2002) Modern organocopper chemistry. Wiley-VCH, Weinheim
Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400
Heaney H, Christie S (2004) Science of synthesis; organometallics, compounds of groups 12 and 11, organometallic complexes of copper. Thieme, Stuttgart, pp 305–662
Tornøe CW, Meldal M (2001) Peptidotriazoles: copper(I)-catalysed 1,3-dipolar cycloadditions on solid phase, Peptides 2001, Proc. Am. Pept. Symp. American Peptide Society and Kluwer Academic Publishers, San Diego, pp 263–264
L’abbé G, Mahy M, Bollyn M, Germain G, Scheefer G (1983) Bull Soc Chim Belg 92:881
Banert K, Hagedorn M (1989) Angew Chem Int Ed 28:1675
Fotsing JR, Banert K (2005) Eur J Org Chem 3704
Bock VD, Hiemstra H, van Maarseveen JH (2006) Eur J Org Chem 51
Meldal M, Tornøe CW (2008) Chem Rev 108:2952
Hein JE, Fokin VV (2010) Chem Soc Rev 39:1302
Ackermann L, Potukuchi HK (2010) Org Biomol Chem 8:4503
Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596
Reddy KR, Rajgopal K, Kantam ML (2006) Synlett 957
Fukuzawa S-i, Shimizu E, Kikuchi S (2007) Synlett 2436
Reddy KR, Rajgopal K, Kantam ML (2007) Catal Lett 114:36
Bonnamour J, Legros J, Crousse B, Bonnet-Delpon D (2007) Tetrahedron Lett 48:8360
Fiandanese V, Bottalico D, Marchese G, Punzi A, Capuzzolo F (2009) Tetrahedron 65:10573
Namitharan K, Kumarraja M, Pitchumani K (2009) Chem Eur J 15:2755
Fiandanese V, Iannone F, Marchese G, Punzi A (2011) Tetrahedron 67:5254
Song YJ, Yoo C, Hong J-T, Kim S-J, Son SU, Jang H-Y (2008) Bull Korean Chem Soc 29:1561
Malkoch M, Schleicher K, Drockenmuller E, Hawker CJ, Russell TP, Wu P, Fokin VV (2005) Macromolecules 38:3663
Ackermann L, Potukuchi HK, Landsberg D, Vicente R (2008) Org Lett 10:3081
Qin A, Lam JWY, Tang L, Jim CJW, Zhao H, Sun J, Tang BZ (2009) Macromolecules 42:1421
Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E (2004) Org Lett 6:4223
Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) J Am Chem Soc 127:210
Urankar D, Košmrlj J (2008) J Comb Chem 10:981
Chandrasekhar S, Seenaiah M, Kumar A, Reddy CR, Mamidyala SK, Kumar CG, Balasubramanian S (2011) Tetrahedron Lett 52:806
Pachón LD, van Maarseveen JH, Rothenberg G (2005) Adv Synth Catal 347:811
Moore E, McInnes SJ, Vogt A, Voelcker NH (2011) Tetrahedron Lett 52:2327
Wang K, Bi X, Xing S, Liao P, Fang Z, Meng X, Zhang Q, Liu Q, Ji Y (2011) Green Chem 13:562
Chassaing S, Kumarraja M, Sido ASS, Pale P, Sommer J (2007) Org Lett 9:883
Chassaing S, Sido ASS, Alix A, Kumarraja M, Pale P, Sommer J (2008) Chem Eur J 14:6713
Yousuf SK, Mukherjee D, Singh B, Maity S, Taneja SC (2010) Green Chem 12:1568
Lipshutz BH, Taft BR (2006) Angew Chem Int Ed 45:8235
Lee C-T, Huang S, Lipshutz BH (2009) Adv Synth Catal 351:3139
Mankad NP, Gray TG, Laitar DS, Sadighi JP (2004) Organometallics 23:1191
Goj LA, Blue ED, Munro-Leighton C, Gunnoe TB, Petersen JL (2005) Inorg Chem 44:8647
Díez-González S, Correa A, Cavallo L, Nolan SP (2006) Chem Eur J 12:7558
Díez-González S, Nolan SP (2008) Angew Chem Int Ed 47:8881
Nolte C, Mayer P, Straub BF (2007) Angew Chem Int Ed 46:2101
Teyssot M-L, Chevry A, Traïkia M, El-Ghozzi M, Avignant D, Gautier A (2009) Chem Eur J 12:6322
Siemsen P, Livingston RC, Diederich F (2000) Angew Chem Int Ed 39:2632
Glaser C (1869) Chem Ber 2:242
Eglinton G, Galbraith AR (1959) J Chem Soc 889
Behr OM, Eglinton G, Galbraith AR, Raphael RA (1960) J Chem Soc 3614
Bohlmann F, Schönowsky H, Inhoffen E, Grau G (1964) Chem Ber 97:794
Fedenok LG, Shvartsberg MS (2011) Tetrahedron Lett 52:3776
Kamata K, Nkaagawa Y, Kotani M, Yamaguchi K, Mizuno N (2008) Angew Chem Int Ed 47:2407
Kamata K, Nkaagawa Y, Tamaguchi K, Mizuno N (2008) J Am Chem Soc 130:15304
Brotherton WS, Michaels HA, Simmons JT, Clark RJ, Dalal NS, Zhu L (2009) Org Lett 11:4954
Rodionov VO, Fokin VV, Finn MG (2005) Angew Chem Int Ed 44:2210
Lewis WG, Magallon FG, Fokin VV, Finn MG (2004) J Am Chem Soc 126:9152
Kasuga K, Ito M, Onoda W, Nakamura Y, Inokuma S, Matsuda T, Nishimura J (2009) Heterocycles 78:963
Olbrich F, Behrens U, Weiss E (1994) J Organomet Chem 472:365
Straub BF (2007) Chem Commun 3868
Ahlquist M, Fokin VV (2007) Organometallics 26:4389
Karlin KD, Hayes JC, Gultneh Y, Cruse RW, McKown JW, Hutchinson JP, Zubieta J (1984) J Am Chem Soc 106:2121
Jin K, Huang X, Pang L, Li J, Appel A, Wherland S (2002) Chem Commun 2872
Huang X-C, Zhang J-P, Chen X-M (2004) J Am Chem Soc 126:13218
Zheng S-L, Messerschmidt M, Coppens P (2005) Angew Chem Int Ed 44:4614
Nast R, Pfab W (1956) Chem Ber 89:415
Blake D, Calvin G, Coates GE (1959) Proc Chem Soc 396
Green MLH (1968) Organometallic compounds, the transition elements, vol 2, 3rd edn. Methuen, London, pp 273–276
Sazonova VA, Kronrod NYa (1956) Zh Obshch Khim 26:1876 (Chem Abstr 1957, 51, 4981c)
Ito H, Arimoto K, Sensui H-o, Hosomi A (1997) Tetrahedron Lett 38:3977
Stephens RD, Castro CE (1963) J Org Chem 28:3313
Atkinson RE, Curtis RF, Taylor JA (1967) J Chem Soc C 578
Owsley DC, Castro CE (1988) Org Synth Coll 6:916
Castro CE, Gaughan EJ, Owsley DC (1966) J Org Chem 31:4071
Chui SSY, Ng MFY, Che C-M (2005) Chem Eur J 11:1739
Yamaguchi K, Oishi T, Katayama T, Mizuno N (2009) Chem Eur J 15:10464
Katayama T, Kamata K, Yamaguchi K, Mizuno N (2009) ChemSusChem 2:59
Buckley BR, Dann SE, Harris DP, Heaney H, Stubbs EC (2010) Chem Commun 46:2274
Chan TR, Hilgraf R, Sharpless KB, Fokin VV (2004) Org Lett 6:2853
Chouhan G, James K (2011) Org Lett 13:2754
Gerard B, Ryan J, Beeler AB, Porco JA Jr (2006) Tetrahedron 62:6405
Knöpfel TF, Carriera EM (2003) J Am Chem Soc 125:6054
Buckley BR, Dann SE, Heaney H (2010) Chem Eur J 16:6278
Shao C, Cheng G, Su D, Xu J, Wang X, Hu Y (2010) Adv Synth Catal 352:1587
Buckley BR, Dann SE, Heaney H, Stubbs EC (2011) Eur J Org Chem 770
Shao C, Zhu R, Luo S, Zhang Q, Wang X, Hu Y (2011) Tetrahedron Lett 52:3782
Shao C, Wang X, Xu J, Zhao J, Zhang Q, Hu Y (2010) J Org Chem 75:7002
Kolb HC, Sharpless KB (2003) Drug Discov Today 8:1128
Fazio F, Bryan MC, Blixt O, Paulson JC, Wong C-H (2002) J Am Chem Soc 124:14387
Speers AE, Adam GC, Cravatt BF (2003) J Am Chem Soc 125:4686
Link AJ, Tirrell DA (2003) J Am Chem Soc 125:11164
Deiters A, Cropp TA, Mukherji M, Chin JW, Anderson JC, Schultz PG (2003) J Am Chem Soc 125:11782
Berrisford DJ, Bolm C, Sharpless KB (1995) Angew Chem Int Ed 34:1059
Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG (2003) J Am Chem Soc 125:3192
Hong V, Udit AK, Evans RA, Finn MG (2008) ChemBioChem 9:1481
Gupta SS, Kuzelka J, Singh P, Lewis WG, Manchester M, Finn MG (2005) Bioconjugate Chem 16:1572
Bergbreiter D, Hamilton PN, Koshti NM (2007) J Am Chem Soc 129:10666
Candelon N, Lastécouères D, Diallo AK, Aranzaes JR, Astruc D, Vincent J-M (2008) Chem Commun 741
Hong V, Presolski SI, Ma C, Finn MG (2009) Angew Chem Int Ed 48:9879
Struthers H, Mindt TL, Schibli R (2010) Dalton Trans 39:675
Lal S, Diez-González S (2011) J Org Chem 76:2367
Wu P, Feldman AK, Nugent AK, Hawker CJ, Scheel A, Voit B, Pyun J, Fréchet JMJ, Sharpless KB, Fokin VV (2004) Angew Chem Int Ed 43:3928
Campbell-Verduyn LS, Mirfeizi L, Dierckx RA, Elsinga PH, Feringa BL (2009) Chem Commun 2139
Gonda Z, Novák Z (2010) Dalton Trans 39:726
Pérez-Balderas F, Ortega-Muñoz M, Morales-Sanfrutos J, Hernández-Mateo F, Calvo-Flores FG, Calvo-Asín JA, Isac-García J, Santoyo-González F (2003) Org Lett 5:1951
Bae I, Han H, Chang S (2005) J Am Chem Soc 127:2038
Kim SH, Jung DY, Chang S (2007) J Org Chem 72:9769
Kim JY, Kim SH, Chang S (2008) Tetrahedron Lett 49:1745
Cassidy MP, Raushel J, Fokin VV (2006) Angew Chem Int Ed 45:3154
Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S (2007) Angew Chem Int Ed 46:1730
Cano I, Nicasio MC, Pérez PJ (2010) Org Biomol Chem 8:536
Yoo EJ, Ahlquist M, Bae I, Sharpless KB, Fokin VV, Chang S (2008) J Org Chem 73:5520
Kim SH, Park SH, Choi JH, Chang S (2011) Chem Asian J 6:2618
Wang F, Fu H, Jiang Y, Zhao Y (2008) Adv Synth Catal 350:1830
Bai S-Q, Koh LL, Hor TSA (2009) Inorg Chem 48:1207
Fabbrizzi P, Cicchi S, Brandi A, Sperotto E, van Koten G (2009) Eur J Org Chem 5423
Zhang S, Zhang D, Liebeskind LS (1997) J Org Chem 62:2312
Raushel J, Fokin VV (2010) Org Lett 12:4952
Kuang G-C, Michaels HA, Simmons JT, Clark RJ, Zhu L (2010) J Org Chem 75:6540
Donnelly PS, Zanatta SD, Zammit SC, White JM, Williams SJ (2008) Chem Commun 2459
Zhou L, Lecourt T, Micouin L (2010) Angew Chem Int Ed 49:2607
Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Angew Chem Int Ed 48:8018
Strieter ER, Bhayana B, Buchwald SL (2009) J Am Chem Soc 131:78
Thorwirth R, Stolle A, Ondruschka B, Wild A, Schubert US (2011) Chem Commun 47:4370
Urankar D, Steinbücher M, Kosjek J, Košmrlj J (2010) Tetrahedron 66:2602
Barz M, Herdtweck E, Thiel WR (1998) Angew Chem Int Ed 37:2262
Brotherton WS, Guha PM, Pan H, Clark RJ, Shatruk M, Zhu L (2011) Dalton Trans 40:3655
Kuang G-C, Guha PM, Brotherton WS, Simmons JT, Stankee LA, Nguyen BT, Clark RJ, Zhu L (2011) J Am Chem Soc 133:13984
Berscheid R, Vögtle F (1992) Synthesis 58
Hansen AE, Ballhausen CJ (1965) Trans Faraday Soc 61:631
Edwards DA, Richards R (1973) J Chem Soc, Dalton Trans 2463
Mounts IC, Ogura T, Fernando Q (1974) Inorg Chem 13:802
Kennedy DC, McKay CS, Legault MCB, Danielson DC, Blake JA, Pegoraro AF, Stolow A, Mester Z, Pezacki JP (2011) J Am Chem Soc 133:17993
Presolski SI, Hong V, Cho S-H, Finn MG (2010) J Am Chem Soc 132:14570
Bogdan AR, James K (2010) Chem Eur J 16:14506
Michaels HA, Zhu L (2011) Chem Asian J 6:2825
Rodionov VO, Presolski SI, Garinier S, Lim Y-H, Finn MG (2007) J Am Chem Soc 129:12696
Rodionov VO, Presolski SI, Díaz DD, Fokin VV, Finn MG (2007) J Am Chem Soc 129:12705
Díez-González S (2011) Catal Sci Technol 1:166
Angell Y, Burgess K (2007) Angew Chem Int Ed 46:3649
Brotherton WS, Guha PM, Phan H, Clark RJ, Shatruk M, Zhu L (2011) Dalton Trans 40:3655–3665
Majumdar KC, Ray K (2011) Synthesis 3787
Acknowledgement
We thank Dr Lei Zhu (University of Florida, Tallahassee) for his valuable comments on an earlier version of this chapter.
Note added in proof An interesting short review on the synthesis of 1,2,3-triazoles involving both thermal (Huisgen) and copper(I) catalysed intramolecular alkyne-azide cycloaddition reactions has appeared [178].
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Buckley, B.R., Heaney, H. (2012). Mechanistic Investigations of Copper(I)-Catalysed Alkyne–Azide Cycloaddition Reactions. In: Košmrlj, J. (eds) Click Triazoles. Topics in Heterocyclic Chemistry, vol 28. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_71
Download citation
DOI: https://doi.org/10.1007/7081_2011_71
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-29428-0
Online ISBN: 978-3-642-29429-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)