CuI-Catalyzed, One-Pot, Three-Component Huisgen Cycloaddition Reaction of Conjugated Enynes and In Situ–Generated Azides

REFERENCES

• (a) Rostovtsev , V. V. ; Green , L. G. ; Fokin , V. V. ; Sharpless , B. K. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes . Angew. Chem., Int. Ed. 2002 , 41 , 2596 – 2599 ; (b) Tornøe , C. W. ; Christensen , C. ; Meldal , M. Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides . J. Org. Chem. 2002 , 67 , 3057 – 3064 .
   PubMed Web of Science ®Google Scholar
• For reviews, see (a) Meldal , M. ; Tornøe , C. W. Cu-catalyzed azide–alkyne cycloaddition. Chem. Rev. 2008, 108, 2952–3015; (b) Spiteri , C. ; Moses , J. E. Copper-catalyzed azide–alkyne cycloaddition: Regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles. Angew. Chem. Int. Ed. 2010, 49, 31–33; (c) Hein , J. E. ; Fokin , V. V. Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: New reactivity of copper(I) acetylides. Chem. Soc. Rev. 2010, 39, 1302–1315; (d) Kappe , C. O. ; der Eycken , E. V. Click chemistry under non-classical reaction conditions. Chem. Soc. Rev. 2010, 39, 1280–1290; (e) Hänni , K. D. ; Leigh , D. A. The application of CuAAC “click” chemistry to catenane and rotaxane synthesis. Chem. Soc. Rev. 2010, 39, 1240–1251; (f) Le Droumaguet , C. ; Wang , C. ; Wang , Q. Fluorogenic click reaction. Chem. Soc. Rev. 2010, 39, 1233–1239; (g) Mamidyala , S. K. ; Finn , M. G. In situ click chemistry: Probing the binding landscapes of biological molecules. Chem. Soc. Rev. 2010, 39, 1252–1261; (h) Holub , J. M. ; Kirshenbaum , K. Tricks with clicks: Modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition. Chem. Soc. Rev. 2010, 39, 1325–1337; (i) Ackermann , L. ; Potukuchi , H. K. Regioselective syntheses of fully-substituted 1,2,3-triazoles: The CuAAC/C–H bond functionalization nexus. Org. Biomol. Chem. 2010, 8, 4503–4513; (j) Gil , M. V. ; Arévalo , M. J. ; López , Ó. Click chemistry—What's in a name? Triazole synthesis and beyond. Synthesis 2007, 1589–1620; (k) Bock , V. D. ; Hiemstra , H. ; van Maarseveen , J. H. CuI-catalyzed alkyne–azide “click” cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 51–68.
   PubMed Web of Science ®Google Scholar
• (a) Wang , Y. ; Liu , J. ; Xia , C. Insights into supported copper(II)-catalyzed azide–alkyne cycloaddition in water . Adv. Synth. Catal. 2011 , 353 , 1534 – 1542 ; (b) Lal , S. ; Díez-González , S. [CuBr(PPh3)3] for azide–alkyne cycloaddition reactions under strict click conditions . J. Org. Chem. 2011 , 76 , 2367 – 2373 ; (c) Friscourt , F. ; Boons , G.-J. One-pot, three-step synthesis of 1,2,3-triazoles by copper-catalyzed cycloaddition of azides with alkynes formed by a Sonogashira cross-coupling and desilylation . Org. Lett. 2010 , 12 , 4936 – 4939 ; (d) Alonso , F. ; Moglie , Y. ; Radivoy , G. ; Yus , M. Multicomponent synthesis of 1,2,3-triazoles in water catalyzed by copper nanoparticles on activated carbon . Adv. Synth. Catal. 2010 , 352 , 3208 – 3214 ; (e) Wang , D. ; Li , N. ; Zhao , M. ; Shi , W. ; Ma , C. ; Chen , B. Solvent-free synthesis of 1,4-disubstituted 1,2,3-triazoles using a low amount of Cu(PPh3)2NO3 complex . Green Chem. 2010 , 12 , 2120 – 2123 ; (f) Yamaguchi , K. ; Kotani , M. ; Kamata , K. ; Mizuno , N. An efficient one-pot, three-component reaction to produce 1,4-disubstituted-1,2,3-triazoles catalyzed by a dicopper-substituted silicotungstate . Chem. Lett. 2008 , 37 , 1258 – 1259 ; (g) Ackermann , L. ; Potukuchi , H. K. ; Landsberg , D. ; Vicente , R. Copper-catalyzed “click” reaction / direct arylation sequence: Modular syntheses of 1,2,3-triazoles . Org. Lett. 2008 , 10 , 3081 – 3084 ; (h) Molander , G. A. ; Ham , J. Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides . Org. Lett. 2006 , 8 , 2767 – 2770 ; (i) Zhang , X. ; Li , H. ; You , L. ; Tang , Y. ; Hsung , R. P. Copper salt–catalyzed azide-[3 + 2] cycloadditions of ynamides and bis-ynamides . Adv. Synth. Catal. 2006 , 348 , 2437 – 2442 ; (j) Odlo , K. ; Høydahl , E. A. ; Hansen , T. V. One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal acetylenes and in situ–generated azides . Tetrahedron Lett. 2007 , 48 , 2097 – 2099 ; (k) Feldman , A. K. ; Colasson , B. ; Fokin , V. V. One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ–generated azides . Org. Lett. 2004 , 6 , 3897 – 3899 ; (l) Appukkuttan , P. ; Dehaen , W. ; Fokin , V. V. ; der Eycken , E. V. A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction . Org. Lett. 2004 , 6 , 4223 – 4225 .
   Google Scholar
• (a) Feldman , A. K. ; Colasson , B. ; Fokin , V. V. One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ–generated azides . Org. Lett. 2004 , 6 , 3897 – 3899 ; (b) Kočalka , P. ; Andersen , N. K. ; Jensen , F. ; Nielsen , P. Synthesis of 5-(1,2,3-triazol-4-yl)-2′-deoxyuridines by a click chemistry approach: Stacking of triazoles in the major groove gives increased nucleic acid duplex stability . Chem. Bio. Chem. 2007 , 8 , 2106 – 2116 ; (c) Zhao , Y.-B. ; Yan , Z.-Y. ; Liang , Y.-M. Efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in ionic liquid/water system . Tetrahedron Lett. 2006 , 47 , 1545 – 1549 .
   PubMed Web of Science ®Google Scholar
• For reviews, see (a) Dieter , R. K. α-Oxo ketene dithioacetals and related compounds: versatile three-carbon synthons . Tetrahedron 1986 , 42 , 3029 – 3096 ; (b) Junjappa , H. ; Ila , H. ; Asokan , C. V. α-Oxoketene-S,S-, N,S-, and N,N-acetals: Versatile intermediates in organic synthesis . Tetrahedron 1990 , 46 , 5423 – 5506 ; (c) Elgemeie , G. H. ; Sayed , S. H. Synthesis and chemistry of dithiols . Synthesis 2001 , 1747 – 1771 ; (d) Pan , L. ; Liu , Q. [5 + 1]-Annulation strategy based on alkenoyl ketene dithioacetals and analogues . Synlett 2011 , 1073 – 1080 .
   Web of Science ®Google Scholar
• (a) Li , Y. ; Xu , X. ; Tan , J. ; Xia , C. ; Zhang , D. ; Liu , Q. Double isocyanide cyclization: A synthetic strategy for two-carbon-tethered pyrrole/oxazole pairs. J. Am. Chem. Soc. 2011, 133, 1775–1777; (b) Tan , J. ; Xu , X. ; Zhang , L. ; Li , Y. ; Liu , Q. Tandem double Michael addition / cyclization / acyl migration of 1,4-dien-3-ones and isocyanoacetate: A new strategy for stereoselective synthesis of pyrrolizidines. Angew. Chem., Int. Ed. 2009, 48, 2868–2872; (c) Wang , H. ; Zhao , Y.-L. ; Ren , C.-Q. ; Diallo , A. ; Liu , Q. Tandem [5 + 1] annulation–isocyanide cyclization: Efficient synthesis of hydroindolones. Chem. Commun. 2011, 47, 12316–12318; (d) Zhao , Y.-L. ; Yang , S.-C. ; Di , C.-H. ; Han , X.-D. ; Liu , Q. Highly efficient synthesis of 3-amino-/alkylthio-cyclobut-2-en-1-ones based on the cyclization of acyl ketene dithioacetals. Chem. Commun. 2010, 46, 7614–7616; (e) Zhao , Y.-L. ; Chen , L. ; Yang , S.-C. ; Tian , C. ; Liu , Q. A synthetic strategy for polyfunctionalized bicyclo[3.3.1]nonanes based on a tandem three-component [3 + 2] cycloaddition of α-cinnamoyl ketene-S,S-acetals with oxalyl chloride. J. Org. Chem. 2009, 74, 5622–5625; (f) Piao , C.-R. ; Zhao , Y.-L. ; Han , X.-D. ; Liu , Q. AlCl3-mediated direct carbon–carbon bond-forming reaction of α-hydroxyketene-S,S-acetals with arenes and synthesis of 3,4-disubstituted dihydrocoumarin derivatives. J. Org. Chem. 2008, 73, 2264–2269; (g) Chen , L. ; Zhao , Y.-L. ; Liu , Q. ; Chen , C. ; Piao , C.-R. Domino reaction of α-acetyl-α-carbamoyl ketene dithioacetals with vilsmeier reagents: A novel and efficient synthesis of 4-halogenated 2(1H)-pyridinones. J. Org. Chem. 2007, 72, 9259–9263.
   PubMed Web of Science ®Google Scholar
• Dong , D. ; Liu , Y. ; Zhao , Y.-L. ; Qi , Y. ; Wang , Z. ; Liu , Q. Vilsmeier–Haack reaction of α-oxo ketene dithioacetals to α-chlorovinyl/ethynyl ketene dithioacetals . Synthesis 2005 , 85 – 91 .
   Google Scholar
• (a) Zhao , Y.-L. ; Liu , Q. ; Zhang , J.-P. ; Liu , Z.-Q. Heteroatom-substituted expanded radialenes: One-pot synthesis and characterization of expanded 1,3-dithiolane[n]radialenes . J. Org. Chem. 2005 , 70 , 6913 – 6917 ; (b) Zhao , Y.-L. ; Zhang , W. ; Zhang , J.-Q. ; Liu , Q. A new route to extended tetrathiafulvalenes from α-acetyl ketene-S,S-acetals . Tetrahedron Lett. 2006 , 47 , 3157 – 3159 .
   PubMed Web of Science ®Google Scholar
• (a) Zhao , Y.-L. ; Li , D.-Z. ; Han , X.-D. ; Chen , L. ; Liu , Q. Proton-promoted hydroamination of 3-dialkylthiomethylene-1,4-pentadiynes with o-phenylenediamines: A facile route to benzo[b] [1,4]diazepines . Adv. Synth. Catal. 2008 , 350 , 1537 – 1543 ; (b) Zhao , Y.-L. ; Liu , Q. ; Zhang , Y.-F. ; Sun , S.-G. ; Li , Y.-N. Chemo- and regioselective addition of carboxylic acid to the alkylthio activated enyne triple bond in the absence of catalysts . Synlett 2006 , 231 – 234 .
   Google Scholar
• Zhao , Y.-L. ; Zhang , W. ; Wang , S. ; Liu , Q. Ethynyl ketene-S,S-acetals: The highly reactive electron-rich dienophiles and applications in the synthesis of 4-functionalized quinolines via a one-pot, three-component reaction . J. Org. Chem. 2007 , 72 , 4985 – 4988 .
   PubMedGoogle Scholar
• Shao , C. ; Wang , X. ; Zhang , Q. ; Luo , S. ; Zhao , J. ; Hu , Y. Acid–base jointly promoted copper(I)-catalyzed azide–alkyne cycloaddition . J. Org. Chem. 2011 , 76 , 6832 – 6836 .
   PubMed Web of Science ®Google Scholar
• Rodionov , V. O. ; Fokin , V. V. ; Finn , M. G. Mechanism of the ligand-free CuI-catalyzed azide–alkyne cycloaddition reaction . Angew. Chem., Int. Ed. 2005 , 44 , 2210 – 2215 .
   PubMed Web of Science ®Google Scholar