Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from Terminal Alkynes

  1. José Ramón Suárez 1
  2. Daniel Collado-Sanz 2
  3. Diego J. Cárdenas 2
  4. Jose Luis Chiara 1
  1. 1 Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
  2. 2 Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
Revista:
Journal of Organic Chemistry

ISSN: 0022-3263,  1520-6904

Ano de publicación: 2015

Volume: 80

Número: 2

Páxinas: 1098-1106

Tipo: Artigo

DOI: 10.1021/JO5025909 GOOGLE SCHOLAR lock_openAcceso aberto editor

Outras publicacións en: Journal of Organic Chemistry

Resumo

Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is extremely fast (<10 min), even at low temperature (−78 °C), and requires substoichiometric amounts of a simple copper(I) or copper(II) salt (2–5 mol %) and an organic base (0.6 mol %). A possible mechanistic pathway is briefly discussed on the basis of model DFT theoretical calculations. The quantitative assessment of the safety of use and shelf stability of nonafluorobutanesulfonyl azide has confirmed that this reagent is a superior and safe alternative to other electrophilic azide reagents in use today.

€ Ver financiamento

Información de financiamento

Financiadores

Referencias bibliográficas

  • Siemsen P., (2000), Angew. Chem., Int. Ed., 39, pp. 2632, 10.1002/1521-3773(20000804)39:15<2632::AID-ANIE2632>3.0.CO;2-F
  • Stefani H. A., (2010), Tetrahedron, 66, pp. 7871, 10.1016/j.tet.2010.07.001
  • Sindhu K. S., (2014), RSC Adv., 4, pp. 27867, 10.1039/C4RA02416H
  • Shi W., (2014), Tetrahedron Lett., 55, pp. 2763, 10.1016/j.tetlet.2014.03.022
  • Glaser C., (1869), Ber. Dtsch. Chem. Ges, 2, pp. 422, 10.1002/cber.186900201183
  • Hay A. S., (1962), J. Org. Chem., 27, pp. 3320, 10.1021/jo01056a511
  • Hay A. S., (1960), J. Org. Chem., 25, pp. 1275, 10.1021/jo01077a633
  • Campbell I. D., (1965), Org. Synth., 45, pp. 39, 10.15227/orgsyn.045.0039
  • Gao H.-Y., (2013), Angew. Chem., Int. Ed., 52, pp. 4024, 10.1002/anie.201208597
  • Petersen T. P., (2012), ChemSusChem, 5, pp. 274, 10.1002/cssc.201100339
  • He Y., (2012), Catal. Sci. Technol., 2, pp. 1126, 10.1039/c2cy20096a
  • Bedard A.-C., (2012), Chem. Commun., 48, pp. 6420, 10.1039/c2cc32464d
  • Alonso F., (2012), ACS Catal., 2, pp. 1441, 10.1021/cs300195r
  • Schmidt R., (2011), Chem.—Eur. J., 17, pp. 8129, 10.1002/chem.201100604
  • Ren Y., (2011), Adv. Synth. Catal., 353, pp. 3473, 10.1002/adsc.201100530
  • Oishi T., (2011), ACS Catal., 1, pp. 1351, 10.1021/cs200388v
  • Kusuda A., (2011), Green Chem., 13, pp. 843, 10.1039/c1gc15106a
  • Jia X., (2011), Green Chem., 13, pp. 2175, 10.1039/c1gc15318h
  • Bedard A.-C., (2011), J. Am. Chem. Soc., 133, pp. 19976, 10.1021/ja208902t
  • Adimurthy S., (2009), J. Org. Chem., 74, pp. 5648, 10.1021/jo900246z
  • Kamata K., (2008), Angew. Chem., Int. Ed., 47, pp. 2407, 10.1002/anie.200705126
  • Jiang H.-F., (2006), Synthesis, pp. 1155, 10.1055/s-2006-926372
  • Chen S.-N., (2009), Green Chem., 11, pp. 269, 10.1039/B815812F
  • Kurita T., (2007), Synlett, pp. 2521
  • Li J.-H., (2005), J. Org. Chem., 70, pp. 4393, 10.1021/jo0503310
  • Batsanov A. S., (2005), J. Org. Chem., 70, pp. 703, 10.1021/jo048428u
  • Fairlamb I. J. S., (2003), Chem. Commun., pp. 632, 10.1039/b212430k
  • Alonso D. A., (2003), Adv. Synth. Catal., 345, pp. 1146, 10.1002/adsc.200303067
  • Krafft M. E., (2001), Tetrahedron Lett., 42, pp. 7733, 10.1016/S0040-4039(01)01701-4
  • Hilt G., (2009), Synthesis, pp. 395, 10.1055/s-0028-1083316
  • Liao Y., (2003), Org. Lett., 5, pp. 909, 10.1021/ol030009g
  • Wang P., (2013), Chin. J. Chem., 31, pp. 187, 10.1002/cjoc.201200878
  • Perez J. M., (2013), Synthesis, 45, pp. 1373, 10.1055/s-0032-1316872
  • Meng X., (2010), Tetrahedron, 66, pp. 4029, 10.1016/j.tet.2010.04.017
  • Chalifoux W. A., (2010), Nat. Chem., 2, pp. 967, 10.1038/nchem.828
  • Rhee I., (1969), Tetrahedron Lett., 10, pp. 4593, 10.1016/S0040-4039(01)88758-X
  • Li P. H., (2004), Chin. Chem. Lett., 15, pp. 1295
  • Crowley J. D., (2010), J. Am. Chem. Soc., 132, pp. 6243, 10.1021/ja101121j
  • Yin W., (2009), Org. Lett., 11, pp. 709, 10.1021/ol8027863
  • Leyva-Perez A., (2012), ACS Catal., 2, pp. 121, 10.1021/cs200532c
  • Peng H., (2014), J. Am. Chem. Soc., 136, pp. 13174, 10.1021/ja5078365
  • Yao P., (2013), J. Chem. Res., 37, pp. 174, 10.3184/174751913X13605921421864
  • Suarez J. R., (2013), Adv. Synth. Catal., 355, pp. 913, 10.1002/adsc.201201001
  • Xu Y., (2001), Tetrahedron, 57, pp. 4337, 10.1016/S0040-4020(01)00376-3
  • Yurieva A. G., (2008), J. Struct. Chem., 49, pp. 548, 10.1007/s10947-008-0073-9
  • Bohlmann F., (1964), Chem. Ber., 97, pp. 794, 10.1002/cber.19640970322
  • Yoo E. J., (2008), J. Org. Chem., 73, pp. 5520, 10.1021/jo800733p
  • Zhu S., (1992), Tetrahedron Lett., 33, pp. 6503, 10.1016/S0040-4039(00)79026-5
  • Zhu S.-Z., (1994), J. Chem. Soc., Perkin Trans. 1, pp. 2077, 10.1039/p19940002077
  • Xu Y., (2000), J. Fluorine Chem., 105, pp. 25, 10.1016/S0022-1139(00)00254-2
  • Xu Y., (2000), Synthesis, pp. 513, 10.1055/s-2000-6360
  • Xu Y., (2001), Synthesis, pp. 690, 10.1055/s-2001-12758
  • Zhu S., (2003), Tetrahedron Lett., 44, pp. 8717, 10.1016/j.tetlet.2003.09.174
  • Zhu S., (2003), Tetrahedron, 59, pp. 4389, 10.1016/S0040-4020(03)00622-7
  • Zhu S.-Z., (2003), J. Fluorine Chem., 120, pp. 65, 10.1016/S0022-1139(02)00290-7
  • He P., (2005), Synthesis, pp. 2137
  • He P., (2005), J. Fluorine Chem., 126, pp. 825, 10.1016/j.jfluchem.2005.03.011
  • Zhu S., (2005), Tetrahedron, 61, pp. 5679, 10.1016/j.tet.2005.03.094
  • Xiong W., (2010), J. Fluorine Chem., 131, pp. 867, 10.1016/j.jfluchem.2010.05.005
  • Xiong W., (2011), Synthesis, pp. 1142
  • Xiong W.-t., (2011), Tetrahedron, 67, pp. 5235, 10.1016/j.tet.2011.05.027
  • Suarez J. R., (2013), Chem. Commun., 49, pp. 9194, 10.1039/c3cc44594a
  • Chiara J. L., (2011), Adv. Synth. Catal., 353, pp. 575, 10.1002/adsc.201000846
  • Suarez J. R., (2010), Adv. Synth. Catal., 352, pp. 2515, 10.1002/adsc.201000417
  • Yekta S., (2007), Synlett, pp. 2069
  • Katritzky A. R., (2010), J. Org. Chem., 75, pp. 6532, 10.1021/jo101296s
  • Kitamura M., (2014), Org. Biomol. Chem., 12, pp. 4397, 10.1039/c4ob00515e
  • Kitamura M., (2011), Eur. J. Org. Chem., 2011, pp. 458, 10.1002/ejoc.201001509
  • Fischer N., (2012), J. Org. Chem., 77, pp. 1760, 10.1021/jo202264r
  • Goddard-Borger E. D., (2007), Org. Lett., 9, pp. 3797, 10.1021/ol701581g
  • Goddard-Borger E. D., (2011), Org. Lett., 13, pp. 2514, 10.1021/ol2007555
  • Trastoy B., (2010), Chem.—Eur. J., 16, pp. 3833, 10.1002/chem.200902422
  • Zhu S.-Z., (1994), J. Chem. Soc., Perkin Trans. 1, pp. 2077, 10.1039/p19940002077
  • Maji M. S., (2008), Angew. Chem., Int. Ed., 47, pp. 9547, 10.1002/anie.200804197
  • Mueller T. J. J., (2003), J. Organomet. Chem., 683, pp. 354, 10.1016/S0022-328X(03)00708-3
  • Ahammed S., (2014), J. Org. Chem., 79, pp. 7391, 10.1021/jo5011069
  • Jiang H.-F., (2007), Synthesis, pp. 1649, 10.1055/s-2007-966058
  • Xiao R., (2012), Eur. J. Org. Chem., 2012, pp. 4178, 10.1002/ejoc.201200359
  • Kang S. H., (2007), Macromolecules, 40, pp. 8349, 10.1021/ma0712293
  • Holmes A. B., (1979), J. Chem. Soc., Chem. Commun., pp. 840, 10.1039/c39790000840
  • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.Gaussian 03, Revision B.03;Gaussian, Inc.:Pittsburgh, PA, 2003.
  • Wadt W. R., (1985), J. Chem. Phys., 82, pp. 284, 10.1063/1.448800
  • Stephens P. J., (1994), J. Phys. Chem., 98, pp. 11623, 10.1021/j100096a001
  • Kohn W., (1996), J. Phys. Chem., 100, pp. 12974, 10.1021/jp960669l
  • Hay P. J., (1985), J. Chem. Phys., 82, pp. 299, 10.1063/1.448975
  • Hay P. J., (1985), J. Chem. Phys., 82, pp. 270, 10.1063/1.448799
  • Becke A. D., (1988), Phys. Rev. A, 38, pp. 3098, 10.1103/PhysRevA.38.3098
  • Lee C., (1988), Phys. Rev. B, 37, pp. 785, 10.1103/PhysRevB.37.785
  • Becke A. D., (1993), J. Chem. Phys., 98, pp. 5648, 10.1063/1.464913