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Mechanistic Investigations of Copper(I)-Catalysed Alkyne–Azide Cycloaddition Reactions

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Click Triazoles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 28))

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.

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References

  1. Biagi G, Giorgi I, Livi O, Scartoni V, Betti L, Giannaccini G, Trincavelli ML (2002) Eur J Med Chem 37:565

    CAS  Google Scholar 

  2. Danence LJT, Gao Y, Li M, Huang H, Wang J (2011) Chem Eur J 17:3584

    CAS  Google Scholar 

  3. Stazi F, Cancogni D, Turco L, Westerduin P, Bacchi S (2010) Tetrahedron Lett 51:5385

    CAS  Google Scholar 

  4. Huisgen R (1961) Proc Chem Soc 357

    Google Scholar 

  5. Husigen R (1963) Angew Chem Int Ed 2:565

    Google Scholar 

  6. Huisgen R (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry, vol 1. Wiley, New York, pp 1–176

    Google Scholar 

  7. Huisgen R, Szeimes G, Möbius L (1967) Chem Ber 100:2494

    CAS  Google Scholar 

  8. Padwa A, Pearson WH (eds) (2003) Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. Wiley, Hoboken, New Jersey

    Google Scholar 

  9. Michael A (1883) J Prakt Chem 48:94

    Google Scholar 

  10. Mitchell G, Rees CW (1987) J Chem Soc Perkin Trans 1 413

    Google Scholar 

  11. Honda K, Nakanishi H, Nagawa Y, Yabe A (1984) J Chem Soc Chem Commun 450

    Google Scholar 

  12. Nagawa Y, Honda K, Nakanishi H (1987) Synthesis 905

    Google Scholar 

  13. Wittig G, Krebs A (1961) Chem Ber 94:3260

    CAS  Google Scholar 

  14. Jewett JC, Bertozzi CR (2010) Chem Soc Rev 39:1272

    CAS  Google Scholar 

  15. Debets MF, van der Doelen CWJ, Rutjes FPJT, van Delft FL (2010) ChemBioChem 11:1168

    CAS  Google Scholar 

  16. Agard NJ, Prescher JA, Bertozzi CR (2004) J Am Chem Soc 126:15046

    CAS  Google Scholar 

  17. 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

    CAS  Google Scholar 

  18. Sletten EM, Nakamura H, Jewett JC, Bertozzi CR (2010) J Am Chem Soc 132:11799

    CAS  Google Scholar 

  19. Plass T, Milles S, Koehler C, Schultz C, Lemke EA (2011) Angew Chem Int Ed 50:3878

    CAS  Google Scholar 

  20. Kirmse W, Horner L (1958) Liebigs Ann Chem 614:1

    CAS  Google Scholar 

  21. Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, Chichester, p 156

    Google Scholar 

  22. Meazza G, Zanardi G (1991) J Fluorine Chem 55:199

    CAS  Google Scholar 

  23. van Berkel SS, Dirks AJ, Meeuwissen SA, Pingen DLL, Boerman OC, Laverman P, van Delft FL, Cornelissen JJLM, Rutjes FPJT (2008) ChemBioChem 9:1805

    Google Scholar 

  24. Huang J, Macdonald SJF, Harrity JPA (2009) Chem Commun 436

    Google Scholar 

  25. Englert BC, Bakbak S, Bunz UHF (2005) Macromolecules 38:5868

    CAS  Google Scholar 

  26. Jiang Y, Kuang C, Yang Q (2011) Tetrahedron 67:289

    CAS  Google Scholar 

  27. Krasinski A, Fokin VV, Sharpless KB (2004) Org Lett 6:1237

    CAS  Google Scholar 

  28. Liu D, Gao W, Dai Q, Zhang X (2005) Org Lett 7:4907

    CAS  Google Scholar 

  29. Dai Q, Gao W, Liu D, Capes LM, Zhang X (2006) J Org Chem 71:3928

    CAS  Google Scholar 

  30. 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

    CAS  Google Scholar 

  31. Chakraborty A, Dey S, Sawoo S, Ardash NN, Sakar A (2010) Organometallics 29:6619

    CAS  Google Scholar 

  32. Heaney H, Ley SV (1973) J Chem Soc Perkin Trans 1 499

    Google Scholar 

  33. Yuan Y, Thomé I, Kim SH, Chen D, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C (2010) Adv Synth Catal 352:2892

    CAS  Google Scholar 

  34. Kwok SW, Fotsing JR, Fraser RJ, Rodionov VO, Fokin VV (2010) Org Lett 12:4217

    CAS  Google Scholar 

  35. Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G (2005) J Am Chem Soc 127:15998

    CAS  Google Scholar 

  36. Rasmussen LK, Boren BC, Fokin VV (2007) Org Lett 9:5337

    CAS  Google Scholar 

  37. Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV (2008) J Am Chem Soc 130:8923

    CAS  Google Scholar 

  38. Lipshutz BH, Sengupta S (1992) Org React 41:135

    CAS  Google Scholar 

  39. Taylor RJK (ed) (1994) Organocopper reagents. Oxford University Press, Oxford

    Google Scholar 

  40. Lipshutz BH (2002) In: Schlosser M (ed) Organometallics in synthesis, a manual. Wiley, Chichester

    Google Scholar 

  41. Krause N (ed) (2002) Modern organocopper chemistry. Wiley-VCH, Weinheim

    Google Scholar 

  42. Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400

    CAS  Google Scholar 

  43. Heaney H, Christie S (2004) Science of synthesis; organometallics, compounds of groups 12 and 11, organometallic complexes of copper. Thieme, Stuttgart, pp 305–662

    Google Scholar 

  44. 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

    Google Scholar 

  45. L’abbé G, Mahy M, Bollyn M, Germain G, Scheefer G (1983) Bull Soc Chim Belg 92:881

    Google Scholar 

  46. Banert K, Hagedorn M (1989) Angew Chem Int Ed 28:1675

    Google Scholar 

  47. Fotsing JR, Banert K (2005) Eur J Org Chem 3704

    Google Scholar 

  48. Bock VD, Hiemstra H, van Maarseveen JH (2006) Eur J Org Chem 51

    Google Scholar 

  49. Meldal M, Tornøe CW (2008) Chem Rev 108:2952

    CAS  Google Scholar 

  50. Hein JE, Fokin VV (2010) Chem Soc Rev 39:1302

    CAS  Google Scholar 

  51. Ackermann L, Potukuchi HK (2010) Org Biomol Chem 8:4503

    CAS  Google Scholar 

  52. Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Google Scholar 

  53. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    CAS  Google Scholar 

  54. Reddy KR, Rajgopal K, Kantam ML (2006) Synlett 957

    Google Scholar 

  55. Fukuzawa S-i, Shimizu E, Kikuchi S (2007) Synlett 2436

    Google Scholar 

  56. Reddy KR, Rajgopal K, Kantam ML (2007) Catal Lett 114:36

    CAS  Google Scholar 

  57. Bonnamour J, Legros J, Crousse B, Bonnet-Delpon D (2007) Tetrahedron Lett 48:8360

    CAS  Google Scholar 

  58. Fiandanese V, Bottalico D, Marchese G, Punzi A, Capuzzolo F (2009) Tetrahedron 65:10573

    CAS  Google Scholar 

  59. Namitharan K, Kumarraja M, Pitchumani K (2009) Chem Eur J 15:2755

    CAS  Google Scholar 

  60. Fiandanese V, Iannone F, Marchese G, Punzi A (2011) Tetrahedron 67:5254

    CAS  Google Scholar 

  61. Song YJ, Yoo C, Hong J-T, Kim S-J, Son SU, Jang H-Y (2008) Bull Korean Chem Soc 29:1561

    CAS  Google Scholar 

  62. Malkoch M, Schleicher K, Drockenmuller E, Hawker CJ, Russell TP, Wu P, Fokin VV (2005) Macromolecules 38:3663

    CAS  Google Scholar 

  63. Ackermann L, Potukuchi HK, Landsberg D, Vicente R (2008) Org Lett 10:3081

    CAS  Google Scholar 

  64. Qin A, Lam JWY, Tang L, Jim CJW, Zhao H, Sun J, Tang BZ (2009) Macromolecules 42:1421

    CAS  Google Scholar 

  65. Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E (2004) Org Lett 6:4223

    CAS  Google Scholar 

  66. Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) J Am Chem Soc 127:210

    CAS  Google Scholar 

  67. Urankar D, Košmrlj J (2008) J Comb Chem 10:981

    CAS  Google Scholar 

  68. Chandrasekhar S, Seenaiah M, Kumar A, Reddy CR, Mamidyala SK, Kumar CG, Balasubramanian S (2011) Tetrahedron Lett 52:806

    CAS  Google Scholar 

  69. Pachón LD, van Maarseveen JH, Rothenberg G (2005) Adv Synth Catal 347:811

    Google Scholar 

  70. Moore E, McInnes SJ, Vogt A, Voelcker NH (2011) Tetrahedron Lett 52:2327

    CAS  Google Scholar 

  71. Wang K, Bi X, Xing S, Liao P, Fang Z, Meng X, Zhang Q, Liu Q, Ji Y (2011) Green Chem 13:562

    CAS  Google Scholar 

  72. Chassaing S, Kumarraja M, Sido ASS, Pale P, Sommer J (2007) Org Lett 9:883

    CAS  Google Scholar 

  73. Chassaing S, Sido ASS, Alix A, Kumarraja M, Pale P, Sommer J (2008) Chem Eur J 14:6713

    CAS  Google Scholar 

  74. Yousuf SK, Mukherjee D, Singh B, Maity S, Taneja SC (2010) Green Chem 12:1568

    CAS  Google Scholar 

  75. Lipshutz BH, Taft BR (2006) Angew Chem Int Ed 45:8235

    CAS  Google Scholar 

  76. Lee C-T, Huang S, Lipshutz BH (2009) Adv Synth Catal 351:3139

    CAS  Google Scholar 

  77. Mankad NP, Gray TG, Laitar DS, Sadighi JP (2004) Organometallics 23:1191

    CAS  Google Scholar 

  78. Goj LA, Blue ED, Munro-Leighton C, Gunnoe TB, Petersen JL (2005) Inorg Chem 44:8647

    CAS  Google Scholar 

  79. Díez-González S, Correa A, Cavallo L, Nolan SP (2006) Chem Eur J 12:7558

    Google Scholar 

  80. Díez-González S, Nolan SP (2008) Angew Chem Int Ed 47:8881

    Google Scholar 

  81. Nolte C, Mayer P, Straub BF (2007) Angew Chem Int Ed 46:2101

    CAS  Google Scholar 

  82. Teyssot M-L, Chevry A, Traïkia M, El-Ghozzi M, Avignant D, Gautier A (2009) Chem Eur J 12:6322

    Google Scholar 

  83. Siemsen P, Livingston RC, Diederich F (2000) Angew Chem Int Ed 39:2632

    CAS  Google Scholar 

  84. Glaser C (1869) Chem Ber 2:242

    Google Scholar 

  85. Eglinton G, Galbraith AR (1959) J Chem Soc 889

    Google Scholar 

  86. Behr OM, Eglinton G, Galbraith AR, Raphael RA (1960) J Chem Soc 3614

    Google Scholar 

  87. Bohlmann F, Schönowsky H, Inhoffen E, Grau G (1964) Chem Ber 97:794

    CAS  Google Scholar 

  88. Fedenok LG, Shvartsberg MS (2011) Tetrahedron Lett 52:3776

    CAS  Google Scholar 

  89. Kamata K, Nkaagawa Y, Kotani M, Yamaguchi K, Mizuno N (2008) Angew Chem Int Ed 47:2407

    CAS  Google Scholar 

  90. Kamata K, Nkaagawa Y, Tamaguchi K, Mizuno N (2008) J Am Chem Soc 130:15304

    CAS  Google Scholar 

  91. Brotherton WS, Michaels HA, Simmons JT, Clark RJ, Dalal NS, Zhu L (2009) Org Lett 11:4954

    CAS  Google Scholar 

  92. Rodionov VO, Fokin VV, Finn MG (2005) Angew Chem Int Ed 44:2210

    CAS  Google Scholar 

  93. Lewis WG, Magallon FG, Fokin VV, Finn MG (2004) J Am Chem Soc 126:9152

    CAS  Google Scholar 

  94. Kasuga K, Ito M, Onoda W, Nakamura Y, Inokuma S, Matsuda T, Nishimura J (2009) Heterocycles 78:963

    Google Scholar 

  95. Olbrich F, Behrens U, Weiss E (1994) J Organomet Chem 472:365

    CAS  Google Scholar 

  96. Straub BF (2007) Chem Commun 3868

    Google Scholar 

  97. Ahlquist M, Fokin VV (2007) Organometallics 26:4389

    CAS  Google Scholar 

  98. Karlin KD, Hayes JC, Gultneh Y, Cruse RW, McKown JW, Hutchinson JP, Zubieta J (1984) J Am Chem Soc 106:2121

    CAS  Google Scholar 

  99. Jin K, Huang X, Pang L, Li J, Appel A, Wherland S (2002) Chem Commun 2872

    Google Scholar 

  100. Huang X-C, Zhang J-P, Chen X-M (2004) J Am Chem Soc 126:13218

    CAS  Google Scholar 

  101. Zheng S-L, Messerschmidt M, Coppens P (2005) Angew Chem Int Ed 44:4614

    CAS  Google Scholar 

  102. Nast R, Pfab W (1956) Chem Ber 89:415

    CAS  Google Scholar 

  103. Blake D, Calvin G, Coates GE (1959) Proc Chem Soc 396

    Google Scholar 

  104. Green MLH (1968) Organometallic compounds, the transition elements, vol 2, 3rd edn. Methuen, London, pp 273–276

    Google Scholar 

  105. Sazonova VA, Kronrod NYa (1956) Zh Obshch Khim 26:1876 (Chem Abstr 1957, 51, 4981c)

    Google Scholar 

  106. Ito H, Arimoto K, Sensui H-o, Hosomi A (1997) Tetrahedron Lett 38:3977

    CAS  Google Scholar 

  107. Stephens RD, Castro CE (1963) J Org Chem 28:3313

    CAS  Google Scholar 

  108. Atkinson RE, Curtis RF, Taylor JA (1967) J Chem Soc C 578

    Google Scholar 

  109. Owsley DC, Castro CE (1988) Org Synth Coll 6:916

    Google Scholar 

  110. Castro CE, Gaughan EJ, Owsley DC (1966) J Org Chem 31:4071

    CAS  Google Scholar 

  111. Chui SSY, Ng MFY, Che C-M (2005) Chem Eur J 11:1739

    CAS  Google Scholar 

  112. Yamaguchi K, Oishi T, Katayama T, Mizuno N (2009) Chem Eur J 15:10464

    CAS  Google Scholar 

  113. Katayama T, Kamata K, Yamaguchi K, Mizuno N (2009) ChemSusChem 2:59

    CAS  Google Scholar 

  114. Buckley BR, Dann SE, Harris DP, Heaney H, Stubbs EC (2010) Chem Commun 46:2274

    CAS  Google Scholar 

  115. Chan TR, Hilgraf R, Sharpless KB, Fokin VV (2004) Org Lett 6:2853

    CAS  Google Scholar 

  116. Chouhan G, James K (2011) Org Lett 13:2754

    CAS  Google Scholar 

  117. Gerard B, Ryan J, Beeler AB, Porco JA Jr (2006) Tetrahedron 62:6405

    CAS  Google Scholar 

  118. Knöpfel TF, Carriera EM (2003) J Am Chem Soc 125:6054

    Google Scholar 

  119. Buckley BR, Dann SE, Heaney H (2010) Chem Eur J 16:6278

    CAS  Google Scholar 

  120. Shao C, Cheng G, Su D, Xu J, Wang X, Hu Y (2010) Adv Synth Catal 352:1587

    CAS  Google Scholar 

  121. Buckley BR, Dann SE, Heaney H, Stubbs EC (2011) Eur J Org Chem 770

    Google Scholar 

  122. Shao C, Zhu R, Luo S, Zhang Q, Wang X, Hu Y (2011) Tetrahedron Lett 52:3782

    CAS  Google Scholar 

  123. Shao C, Wang X, Xu J, Zhao J, Zhang Q, Hu Y (2010) J Org Chem 75:7002

    CAS  Google Scholar 

  124. Kolb HC, Sharpless KB (2003) Drug Discov Today 8:1128

    CAS  Google Scholar 

  125. Fazio F, Bryan MC, Blixt O, Paulson JC, Wong C-H (2002) J Am Chem Soc 124:14387

    Google Scholar 

  126. Speers AE, Adam GC, Cravatt BF (2003) J Am Chem Soc 125:4686

    CAS  Google Scholar 

  127. Link AJ, Tirrell DA (2003) J Am Chem Soc 125:11164

    CAS  Google Scholar 

  128. Deiters A, Cropp TA, Mukherji M, Chin JW, Anderson JC, Schultz PG (2003) J Am Chem Soc 125:11782

    CAS  Google Scholar 

  129. Berrisford DJ, Bolm C, Sharpless KB (1995) Angew Chem Int Ed 34:1059

    CAS  Google Scholar 

  130. Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG (2003) J Am Chem Soc 125:3192

    CAS  Google Scholar 

  131. Hong V, Udit AK, Evans RA, Finn MG (2008) ChemBioChem 9:1481

    CAS  Google Scholar 

  132. Gupta SS, Kuzelka J, Singh P, Lewis WG, Manchester M, Finn MG (2005) Bioconjugate Chem 16:1572

    Google Scholar 

  133. Bergbreiter D, Hamilton PN, Koshti NM (2007) J Am Chem Soc 129:10666

    CAS  Google Scholar 

  134. Candelon N, Lastécouères D, Diallo AK, Aranzaes JR, Astruc D, Vincent J-M (2008) Chem Commun 741

    Google Scholar 

  135. Hong V, Presolski SI, Ma C, Finn MG (2009) Angew Chem Int Ed 48:9879

    CAS  Google Scholar 

  136. Struthers H, Mindt TL, Schibli R (2010) Dalton Trans 39:675

    CAS  Google Scholar 

  137. Lal S, Diez-González S (2011) J Org Chem 76:2367

    CAS  Google Scholar 

  138. 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

    CAS  Google Scholar 

  139. Campbell-Verduyn LS, Mirfeizi L, Dierckx RA, Elsinga PH, Feringa BL (2009) Chem Commun 2139

    Google Scholar 

  140. Gonda Z, Novák Z (2010) Dalton Trans 39:726

    CAS  Google Scholar 

  141. 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

    Google Scholar 

  142. Bae I, Han H, Chang S (2005) J Am Chem Soc 127:2038

    CAS  Google Scholar 

  143. Kim SH, Jung DY, Chang S (2007) J Org Chem 72:9769

    CAS  Google Scholar 

  144. Kim JY, Kim SH, Chang S (2008) Tetrahedron Lett 49:1745

    CAS  Google Scholar 

  145. Cassidy MP, Raushel J, Fokin VV (2006) Angew Chem Int Ed 45:3154

    CAS  Google Scholar 

  146. Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S (2007) Angew Chem Int Ed 46:1730

    CAS  Google Scholar 

  147. Cano I, Nicasio MC, Pérez PJ (2010) Org Biomol Chem 8:536

    CAS  Google Scholar 

  148. Yoo EJ, Ahlquist M, Bae I, Sharpless KB, Fokin VV, Chang S (2008) J Org Chem 73:5520

    CAS  Google Scholar 

  149. Kim SH, Park SH, Choi JH, Chang S (2011) Chem Asian J 6:2618

    CAS  Google Scholar 

  150. Wang F, Fu H, Jiang Y, Zhao Y (2008) Adv Synth Catal 350:1830

    CAS  Google Scholar 

  151. Bai S-Q, Koh LL, Hor TSA (2009) Inorg Chem 48:1207

    CAS  Google Scholar 

  152. Fabbrizzi P, Cicchi S, Brandi A, Sperotto E, van Koten G (2009) Eur J Org Chem 5423

    Google Scholar 

  153. Zhang S, Zhang D, Liebeskind LS (1997) J Org Chem 62:2312

    CAS  Google Scholar 

  154. Raushel J, Fokin VV (2010) Org Lett 12:4952

    CAS  Google Scholar 

  155. Kuang G-C, Michaels HA, Simmons JT, Clark RJ, Zhu L (2010) J Org Chem 75:6540

    CAS  Google Scholar 

  156. Donnelly PS, Zanatta SD, Zammit SC, White JM, Williams SJ (2008) Chem Commun 2459

    Google Scholar 

  157. Zhou L, Lecourt T, Micouin L (2010) Angew Chem Int Ed 49:2607

    CAS  Google Scholar 

  158. Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Angew Chem Int Ed 48:8018

    CAS  Google Scholar 

  159. Strieter ER, Bhayana B, Buchwald SL (2009) J Am Chem Soc 131:78

    CAS  Google Scholar 

  160. Thorwirth R, Stolle A, Ondruschka B, Wild A, Schubert US (2011) Chem Commun 47:4370

    CAS  Google Scholar 

  161. Urankar D, Steinbücher M, Kosjek J, Košmrlj J (2010) Tetrahedron 66:2602

    CAS  Google Scholar 

  162. Barz M, Herdtweck E, Thiel WR (1998) Angew Chem Int Ed 37:2262

    CAS  Google Scholar 

  163. Brotherton WS, Guha PM, Pan H, Clark RJ, Shatruk M, Zhu L (2011) Dalton Trans 40:3655

    CAS  Google Scholar 

  164. Kuang G-C, Guha PM, Brotherton WS, Simmons JT, Stankee LA, Nguyen BT, Clark RJ, Zhu L (2011) J Am Chem Soc 133:13984

    CAS  Google Scholar 

  165. Berscheid R, Vögtle F (1992) Synthesis 58

    Google Scholar 

  166. Hansen AE, Ballhausen CJ (1965) Trans Faraday Soc 61:631

    CAS  Google Scholar 

  167. Edwards DA, Richards R (1973) J Chem Soc, Dalton Trans 2463

    Google Scholar 

  168. Mounts IC, Ogura T, Fernando Q (1974) Inorg Chem 13:802

    CAS  Google Scholar 

  169. 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

    CAS  Google Scholar 

  170. Presolski SI, Hong V, Cho S-H, Finn MG (2010) J Am Chem Soc 132:14570

    CAS  Google Scholar 

  171. Bogdan AR, James K (2010) Chem Eur J 16:14506

    CAS  Google Scholar 

  172. Michaels HA, Zhu L (2011) Chem Asian J 6:2825

    CAS  Google Scholar 

  173. Rodionov VO, Presolski SI, Garinier S, Lim Y-H, Finn MG (2007) J Am Chem Soc 129:12696

    CAS  Google Scholar 

  174. Rodionov VO, Presolski SI, Díaz DD, Fokin VV, Finn MG (2007) J Am Chem Soc 129:12705

    CAS  Google Scholar 

  175. Díez-González S (2011) Catal Sci Technol 1:166

    Google Scholar 

  176. Angell Y, Burgess K (2007) Angew Chem Int Ed 46:3649

    CAS  Google Scholar 

  177. Brotherton WS, Guha PM, Phan H, Clark RJ, Shatruk M, Zhu L (2011) Dalton Trans 40:3655–3665

    Google Scholar 

  178. Majumdar KC, Ray K (2011) Synthesis 3787

    Google Scholar 

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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].

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Correspondence to Harry Heaney .

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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

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