Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2008(1): 141-148
DOI: 10.1055/s-2007-990943
DOI: 10.1055/s-2007-990943
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New YorkStudy of Copper(I) Catalysts for the Synthesis of Carbanucleosides via Azide-Alkyne 1,3-Dipolar Cycloaddition
Further Information
Received
22 October 2007
Publication Date:
07 December 2007 (online)
Publication History
Publication Date:
07 December 2007 (online)
Abstract
The activity of three copper(I)-based catalytic systems in the preparation of various 1,2,3-triazolyl-carbanucleosides via the Huisgen azide-alkyne 1,3-dipolar cycloaddition is presented. The influence of the alkyne substituent, solvent, and heating mode were studied. The preparation of [1,2-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]bromocopper [(IMes)CuBr] is discussed.
Key words
copper(I) catalysts - Huisgen 1,3-dipolar cycloaddition - carbanucleosides - N-heterocyclic carbenes
- 1a
Huisgen R. Angew. Chem., Int. Ed. Engl. 1963, 2: 565 - 1b
Huisgen R. In 1,3-Dipolar Cycloaddition Chemistry Vol. 1:Padwa A. Wiley; New York: 1984. - 2a
Gilchrist TL.Gymer GE. Adv. Heterocycl. Chem. 1974, 16: 33 - 2b
Finley KT. The Chemistry of Heterocyclic Compounds Vol. 39: Wiley; New York: 1980. p.349 - 2c
Katritzky AR.Zhang Y.Singh SK. Heterocycles 2003, 60: 1225 - For therapeutic activities see:
- 2d
Buckle DR.Rockell CJM.Smith H.Spicer BA. J. Med. Chem. 1986, 29: 2262 - 2e
Alvarez R.Velazquez S.San-Felix A.Aquaro S.De Clercq E.Perno CF.Karlsson A.Balzarini J.Camarasa MJ. J. Med. Chem. 1994, 37: 4185 - 2f
Chen MD.Lu SJ.Yuag GP.Yang SY.Du XL. Heterocycl. Commun. 2000, 6: 421 - 2g
Genin MJ.Allwine DA.Anderson DJ.Barbachyn MR.Emmert DE.Garmon SA.Graber DR.Grega KC.Hester JB.Hutchinson DK.Morris J.Reischer RJ.Ford CW.Zurenko GE.Hamel JC.Schaadt RD.Stapert D.Yagi BH. J. Med. Chem. 2000, 43: 953 - 3
Wang Q.Chittaboina S.Barnhill HN. Lett. Org. Chem. 2005, 2: 293 - 4
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596Reference Ris Wihthout Link - 5
Tornøe CW.Christensen C.Meldal M. J. Org. Chem. 2002, 67: 3057 - 6
Kolb HC.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 - 7
Kolb HC.Sharpless KB. Drug Discovery Today 2003, 8: 1128 - 8a
Alonso R.Camarasa MJ.Alonso G.de las Heras FG. Eur. J. Med. Chem. 1980, 15: 105 - 8b
Velazquez S.Alvarez R.Perez C.Gago F.De Clercq E.Balzarini J.Camarasa MJ. Antiviral Chem. Chemother. 1998, 9: 481 - 8c
Saito Y.Escuret V.Durantel D.Zoulim F.Schinazi RF.Agrofoglio LA. Bioorg. Med. Chem. 2003, 11: 3633 - 9a
San-Felix A.Alvarez R.Velazquez S.De Clercq E.Balzarini J.Camarasa MJ. Nucleosides Nucleotides 1995, 14: 595 - 9b
Yamashita M.Mallikarjuna Reddy P.Kato Y.Krishna Reddy V.Suzuki K.Oshikawa T. Carbohydr. Res. 2001, 336: 257 - 9c
Lazrek HB.Taourirte M.Oulih T.Barascut JL.Imbach JL.Pannecouque C.Witrouw M.De Clercq E. Nucleosides, Nucleotides Nucleic Acids 2001, 20: 1949 - 9d
Joubert N.Schinazi RF.Agrofoglio LA. Tetrahedron 2005, 61: 11744 - 9e
Guezguez R.Bougrin K.El Akri K.Benhida R. Tetrahedron Lett. 2006, 47: 4807 - 10
Himo F.Lovell T.Hilgraf R.Rostovtsev VV.Noodleman L.Sharpless KB.Fokin VV. J. Am. Chem. Soc. 2005, 127: 210 - 11
Quader S.Boyd SE.Jenkins ID.Houston TA. J. Org. Chem. 2007, 72: 1962 - 12a
Durán Pachón L.Van Maarseveen JH.Rothenberg R. Adv. Synth. Catal. 2005, 347: 811 - 12b
Aucagne V.Hänni KD.Leigh DA.Lusby PJ.Walker DB. J. Am. Chem. Soc. 2006, 128: 2186 - 12c
Lipshutz BH.Taft BR. Angew. Chem. Int. Ed. 2006, 45: 8235 - 12d
Chassaing S.Kumarraja M.Sani Souna Sido A.Pale P.Sommer J. Org. Lett. 2007, 9: 883 - 13
Aucagne V.Leigh DA. Org. Lett. 2006, 8: 4505 - 14
Feng L.Zhang X.Yu Z.Wang J.Gu Z. Chem. Mater. 2002, 14: 4021 - For the copper-catalyzed coupling of terminal alkynes (i.e., the Glaser reaction), see:
- 15a
Glaser C. Ber. Dtsch. Chem Ges. 1869, 2: 422Reference Ris Wihthout Link - 15b
Glaser C. Ann. Chem. Pharm. 1870, 154: 137Reference Ris Wihthout Link - 15c
Siemsen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632Reference Ris Wihthout Link - 16a
Pérez-Balderas F.Ortega-Muñoz M.Morales-Sanfrutos J.Hernández-Mateo F.Calvo-Flores FG.Calvo-Asín JA.Isac-García J.Santoyo-González F. Org. Lett. 2003, 5: 1951 - 16b
Chan TR.Hilgraf R.Sharpless KB.Fokin VV. Org. Lett. 2004, 6: 2853 - 16c
Meng J.Fokin VV.Finn MG. Tetrahedron Lett. 2005, 46: 4543 - 16d
Gerard B.Ryan J.Beeler AB.Porco JA. Tetrahedron 2006, 62: 6405 - For recent reviews on NHC ligands, see:
- 17a
N-Heterocyclic Carbenes in Synthesis
Nolan SP. Wiley-VCH; Weinheim: 2006.Reference Ris Wihthout Link - 17b
N-Heterocyclic Carbenes in Transition Metal Catalysis
Glorius F. Springer; Berlin: 2007.Reference Ris Wihthout Link - 18
Díez-González S.Nolan SP. Synlett 2007, 2158 - 19
Lebel H.Davi D.Díez-González S.Nolan SP. J. Org. Chem. 2007, 72: 144 - 20a
Kaur H.Zinn FK.Stevens ED.Nolan SP. Organometallics 2004, 23: 1157 - 20b
Díez-González S.Scott NM.Nolan SP. Organometallics 2006, 25: 2355 - 21
Fructos MR.Belderrain TR.Nicasio MC.Nolan SP.Kaur H.Díaz-Requejo MM.Pérez PJ. J. Am. Chem. Soc. 2004, 126: 10846 - 22
Díez-González S.Correa A.Cavallo L.Nolan SP. Chem. Eur. J. 2006, 12: 7558 - 23
Díez-González S.Kaur H.Zinn FK.Stevens ED.Nolan SP. J. Org. Chem. 2005, 70: 4784 - For representative examples, see:
- 25a
Mankad NP.Gray TG.Laitar DS.Sadighi JP. Organometallics 2004, 23: 1191 - 25b
Goj LA.Blue ED.Delp SA.Gunnoe TB.Cundari TR.Petersen JL. Organometallics 2006, 25: 4097 ; see also ref. 20a and 23 - 26
Depres JP.Greene AE. J. Org. Chem. 1984, 49: 928 - 27
Paulsen H.Maass U. Chem. Ber. 1981, 114: 346 - For reviews on microwave-assisted reactions see:
- 28a
Caddick S. Tetrahedron 1995, 51: 10403 - 28b
Perreux L.Loupy A. Tetrahedron 2001, 57: 9199 - 28c
Microwaves in Organic Synthesis
Loupy A. Wiley-VCH; Weinheim: 2002. - 28d
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 - 29a
Louërat F.Bougrin K.Loupy A.Ochoa de Retana AM.Pagalday J.Palacios F. Heterocycles 1998, 48: 161 - 29b
Rijkers DTS.Van Esse GW.Merkx R.Brouwer AJ.Jacobs HJF.Pieters RJ.Liskamp RMJ. Chem. Commun. 2005, 4581 - 29c
Perissutti E.Frecentese F.Fiorino F.Severino B.Cirillo D.Santagada V.Caliendo G. J. Heterocycl. Chem. 2007, 44: 815 - See also:
- 29d
Appukkuttan P.Dehaen W.Fokin VV.Van der Eycken E. Org. Lett. 2004, 6: 4223 - For mechanistic studies on CuAAC, see:
- 30a
Rodionov VO.Fokin VV.Finn MG. Angew. Chem. Int. Ed. 2005, 44: 2210 - 30b
Nolte C.Mayer P.Straub BF. Angew. Chem. Int. Ed. 2007, 46: 2001 ; see also ref. 10 - 32
Katritzky AR.Singh SK. J. Org. Chem. 2002, 67: 9077 - 33
Bock VD.Hiemstra H.van Maarseveen JH. Eur. J. Org. Chem. 2005, 51 - 34
Trost BM.Ball ZT.Jöge TA. J. Am. Chem. Soc. 2002, 124: 7922
References
File CCDC 654537 contains the complete crystallographic data for (IMes)CuBr. These data can be obtained free of charge from The Cambridge Crystallographic Data center via www.ccdc.cam.ac.uk/data-request/cif.
31Ratio 1,4-triazole/1,5-triazole = 65:35.