SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 52, Issue 50, 2013, Pages 13468-13471

Gold-catalyzed synthesis of tetrazoles from alkynes by Cï£ ¿C bond cleavage

(2) Gaydou, Morgane a,b Echavarren, Antonio M a

a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ (Spain)

b UNIVERSITAT ROVIRA I VIRGILI (Spain)

Author keywords

azides; cycloadditions; gold; heterocycles; rearrangement

Indexed keywords

AZIDES; BOND CLEAVAGES; CYCLOADDITIONS; DUAL ROLE; HETEROCYCLES; REARRANGEMENT; TETRAZOLES; TRIMETHYLSILYL;

HYDROCARBONS;

GOLD;

EID: 84889663717 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201308076 Document Type: Article

Times cited : (63)

References (68)

1
- 0002641899
- R. Huisgen, Proc. Chem. Soc. 1961, 357-396
- (1961) Proc. Chem. Soc. , pp. 357-396
- Huisgen, R.¹

2
- 0001427691
- R. Huisgen, Angew. Chem. 1963, 75, 604-637
- (1963) Angew. Chem. , vol.75 , pp. 604-637
- Huisgen, R.¹

3
- 36749014055
- Angew. Chem. Int. Ed. Engl. 1963, 2, 565-598.
- (1963) Angew. Chem. Int. Ed. Engl. , vol.2 , pp. 565-598

4
- 0000749443
- H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
- (2001) Angew. Chem. , vol.113 , pp. 2056-2075
- Kolb, H.C.¹ Finn, M.G.² Sharpless, K.B.³

5
- 0000096835
- Angew. Chem. Int. Ed. 2001, 40, 2004-2021
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2004-2021

6
- 0013064237
- V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
- (2002) Angew. Chem. , vol.114 , pp. 2708-2711
- Rostovtsev, V.¹ Green, L.G.² Fokin, V.V.³ Sharpless, K.B.⁴

7
- 0037099395
- Angew. Chem. Int. Ed. 2002, 41, 2596-2599
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2596-2599

8
- 77949796395
- J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1302-1315
- (2010) Chem. Soc. Rev. , vol.39 , pp. 1302-1315
- Hein, J.E.¹ Fokin, V.V.²

9
- 84876676322
- B. T. Worrell, J. A. Malik, V. V. Fokin, Science 2013, 340, 457-460.
- (2013) Science , vol.340 , pp. 457-460
- Worrell, B.T.¹ Malik, J.A.² Fokin, V.V.³

10
- 51049094897
- M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952-3015.
- (2008) Chem. Rev. , vol.108 , pp. 2952-3015
- Meldal, M.¹ Tornøe, C.W.²

11
- 28044465418
- L. Zhang, X. Chen, P. Xue, H. H. Y. Sun, I. D. Williams, K. B. Sharpless, V. V. Fokin, G. Jia, J. Am. Chem. Soc. 2005, 127, 15998-15999
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 15998-15999
- Zhang, L.¹ Chen, X.² Xue, P.³ Sun, H.H.Y.⁴ Williams, I.D.⁵ Sharpless, K.B.⁶ Fokin, V.V.⁷ Jia, G.⁸

12
- 38349168748
- L. K. Rasmussen, B. C. Boren, V. V. Fokin, Org. Lett. 2007, 9, 5337-5339
- (2007) Org. Lett. , vol.9 , pp. 5337-5339
- Rasmussen, L.K.¹ Boren, B.C.² Fokin, V.V.³

13
- 47349098606
- B. C. Boren, S. Narayan, L. K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 8923-8930.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8923-8930
- Boren, B.C.¹ Narayan, S.² Rasmussen, L.K.³ Zhang, L.⁴ Zhao, H.⁵ Lin, Z.⁶ Jia, G.⁷ Fokin, V.V.⁸

14
- 83755219563
- J. McNulty, K. Keskar, R. Vemula, Chem. Eur. J. 2011, 17, 14727-14730
- (2011) Chem. Eur. J. , vol.17 , pp. 14727-14730
- McNulty, J.¹ Keskar, K.² Vemula, R.³

15
- 84866510737
- J. McNulty, K. Keskar, Eur. J. Org. Chem. 2012, 5462-5470.
- (2012) Eur. J. Org. Chem. , pp. 5462-5470
- McNulty, J.¹ Keskar, K.²

16
- 84884537227
- E. Rasolofonjatovo, S. Theeramunkong, A. Bouriaud, S. Kolodych, M. Chaumontet, F. Taran, Org. Lett. 2013, 15, 4698-4701.
- (2013) Org. Lett. , vol.15 , pp. 4698-4701
- Rasolofonjatovo, E.¹ Theeramunkong, S.² Bouriaud, A.³ Kolodych, S.⁴ Chaumontet, M.⁵ Taran, F.⁶

17
- 84884550827
- C. D. Smith, M. F. Greaney, Org. Lett. 2013, 15, 4826-4829.
- (2013) Org. Lett. , vol.15 , pp. 4826-4829
- Smith, C.D.¹ Greaney, M.F.²

18
- 85043763626
- Triazoles are formed in the reaction of azides with terminal alkynes in the presence of nanoporous titania-supported gold nanoparticles: M. Boominathan, N. Pugazhenthiran, M. Nagaraj, S. Muthusubramanian, S. Murugesan, N. Bhuvanesh, ACS Sustainable Chem. Eng. 2013, DOI:.
- (2013) ACS Sustainable Chem. Eng.
- Boominathan, M.¹ Pugazhenthiran, N.² Nagaraj, M.³ Muthusubramanian, S.⁴ Murugesan, S.⁵ Bhuvanesh, N.⁶

19
- 84885613695
- T. Shen, T. Wang, C. Qin, N. Jiao, Angew. Chem. 2013, 125, 6809-6812
- (2013) Angew. Chem. , vol.125 , pp. 6809-6812
- Shen, T.¹ Wang, T.² Qin, C.³ Jiao, N.⁴

20
- 84879351373
- Angew. Chem. Int. Ed. 2013, 52, 6677-6680.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 6677-6680

21
- 84889648482
- C. Qin, P. Feng, Y. Ou, T. Shen, T. Wang, N. Jiao, Angew. Chem. 2013, 125, 8004-8008
- (2013) Angew. Chem. , vol.125 , pp. 8004-8008
- Qin, C.¹ Feng, P.² Ou, Y.³ Shen, T.⁴ Wang, T.⁵ Jiao, N.⁶

22
- 84880395260
- Angew. Chem. Int. Ed. 2013, 52, 7850-7854.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 7850-7854

23
- 0012698954
- P. A. S. Smith, J. Am. Chem. Soc. 1948, 70, 320-323.
- (1948) J. Am. Chem. Soc. , vol.70 , pp. 320-323
- Smith, P.A.S.¹

24
- 0008154003
- L. E. Fikes, H. Shechter, J. Org. Chem. 1979, 44, 741-744
- (1979) J. Org. Chem. , vol.44 , pp. 741-744
- Fikes, L.E.¹ Shechter, H.²

25
- 0001183472
- G. L. Milligan, C. J. Mossman, J. Aubé, J. Am. Chem. Soc. 1995, 117, 10449-10459
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 10449-10459
- Milligan, G.L.¹ Mossman, C.J.² Aubé, J.³

26
- 84855560621
- O. Gutierrez, J. Aubé, D. J. Tantillo, J. Org. Chem. 2012, 77, 640-647.
- (2012) J. Org. Chem. , vol.77 , pp. 640-647
- Gutierrez, O.¹ Aubé, J.² Tantillo, D.J.³

27
- 84879377941
- F. Chen, C. Qin, Y. Cui, N. Jiao, Angew. Chem. 2011, 123, 11689-11693
- (2011) Angew. Chem. , vol.123 , pp. 11689-11693
- Chen, F.¹ Qin, C.² Cui, Y.³ Jiao, N.⁴

28
- 81755187244
- Angew. Chem. Int. Ed. 2011, 50, 11487-11491.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 11487-11491

29
- 84879235342
- N. Okamoto, M. Ishikura, R. Yanada, Org. Lett. 2013, 15, 2571-2573.
- (2013) Org. Lett. , vol.15 , pp. 2571-2573
- Okamoto, N.¹ Ishikura, M.² Yanada, R.³

30
- 18244399612
- C. Nieto-Oberhuber, S. Lõpez, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 6178-6179
- Nieto-Oberhuber, C.¹ Lõpez, S.² Echavarren, A.M.³

31
- 34250826150
- E. Herrero-Gõmez, C. Nieto-Oberhuber, S. Lõpez, J. Benet-Buchholz, A. M. Echavarren, Angew. Chem. 2006, 118, 5581-5585
- (2006) Angew. Chem. , vol.118 , pp. 5581-5585
- Herrero-Gõmez, E.¹ Nieto-Oberhuber, C.² Lõpez, S.³ Benet-Buchholz, J.⁴ Echavarren, A.M.⁵

32
- 33748659666
- Angew. Chem. Int. Ed. 2006, 45, 5455-5459
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 5455-5459

33
- 77951967603
- P. Pérez-Galán, N. Delpont, E. Herrero-Gõmez, F. Maseras, A. M. Echavarren, Chem. Eur. J. 2010, 16, 5324-5332.
- (2010) Chem. Eur. J. , vol.16 , pp. 5324-5332
- Pérez-Galán, P.¹ Delpont, N.² Herrero-Gõmez, E.³ Maseras, F.⁴ Echavarren, A.M.⁵

34
- 84871569403
- 3 and generation of hydrazoic acid, see:, F. González-Bobes, N. Kopp, L. Li, J. Deerberg, P. Sharma, S. Leung, M. Davies, J. Bush, J. Hamm, M. Hrytsak, Org. Process Res. Dev. 2012, 16, 2051-2057.
- (2012) Org. Process Res. Dev. , vol.16 , pp. 2051-2057
- González-Bobes, F.¹ Kopp, N.² Li, L.³ Deerberg, J.⁴ Sharma, P.⁵ Leung, S.⁶ Davies, M.⁷ Bush, J.⁸ Hamm, J.⁹ Hrytsak, M.¹⁰

35
- 84889655940
- CCDC960733 (9 a), CCDC960734 (9 b), CCDC960735 (9 c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre
- CCDC960733 (9 a), CCDC960734 (9 b), CCDC960735 (9 c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

36
- 84856725223
- 5)Au(1-benzyltetrazole)], in which the tretrazole is also bound through 4N:, W. F. Gabrielli, S. D. Nogai, M. Nell, S. Cronje, H. G. Raubenheimer, Polyhedron 2012, 34, 188-197.
- (2012) Polyhedron , vol.34 , pp. 188-197
- Gabrielli, W.F.¹ Nogai, S.D.² Nell, M.³ Cronje, S.⁴ Raubenheimer, H.G.⁵

37
- 32944466327
- C. Nieto-Oberhuber, S. Lõpez, M. P. Muñoz, D. J. Cárdenas, E. Buñuel, C. Nevado, A. M. Echavarren, Angew. Chem. 2005, 117, 6302-6304
- (2005) Angew. Chem. , vol.117 , pp. 6302-6304
- Nieto-Oberhuber, C.¹ Lõpez, S.² Muñoz, M.P.³ Cárdenas, D.J.⁴ Buñuel, E.⁵ Nevado, C.⁶ Echavarren, A.M.⁷

38
- 25844453872
- Angew. Chem. Int. Ed. 2005, 44, 6146-6148
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6146-6148

39
- 84874585261
- C. Obradors, A. M. Echavarren, Chem. Eur. J. 2013, 19, 3547-3551
- (2013) Chem. Eur. J. , vol.19 , pp. 3547-3551
- Obradors, C.¹ Echavarren, A.M.²

40
- 84889682755
- A. Homs, C. Obradors, D. Leboeuf, A.M. Echavarren, submitted
- A. Homs, C. Obradors, D. Leboeuf, A.M. Echavarren, submitted.

41
- 33947301041
- G. L'abbé, Chem. Rev. 1969, 69, 345-363
- (1969) Chem. Rev. , vol.69 , pp. 345-363
- L'Abbé, G.¹

42
- 33845278154
- E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368.
- (1988) Chem. Rev. , vol.88 , pp. 297-368
- Scriven, E.F.V.¹ Turnbull, K.²

43
- 0000323429
- D. N. Kevill, F. L. Weitl, J. Org. Chem. 1970, 35, 2526-2529
- (1970) J. Org. Chem. , vol.35 , pp. 2526-2529
- Kevill, D.N.¹ Weitl, F.L.²

44
- 0001505608
- L. A. Lee, R. Evans, J. W. Wheeler, J. Org. Chem. 1972, 37, 343-347.
- (1972) J. Org. Chem. , vol.37 , pp. 343-347
- Lee, L.A.¹ Evans, R.² Wheeler, J.W.³

45
- 70350004081
- D. Weber, M. A. Tarselli, M. R. Gagné, Angew. Chem. 2009, 121, 5843-5846
- (2009) Angew. Chem. , vol.121 , pp. 5843-5846
- Weber, D.¹ Tarselli, M.A.² Gagné, M.R.³

46
- 70349904871
- Angew. Chem. Int. Ed. 2009, 48, 5733-5736
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5733-5736

47
- 71049178710
- D. Weber, M. R. Gagné, Org. Lett. 2009, 11, 4962-4965
- (2009) Org. Lett. , vol.11 , pp. 4962-4965
- Weber, D.¹ Gagné, M.R.²

48
- 79952266862
- G. Seidel, C. W. Lehmann, A. Fürstner, Angew. Chem. 2010, 122, 8644-8648
- (2010) Angew. Chem. , vol.122 , pp. 8644-8648
- Seidel, G.¹ Lehmann, C.W.² Fürstner, A.³

49
- 78149425384
- Angew. Chem. Int. Ed. 2010, 49, 8466-8470
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8466-8470

50
- 84862681730
- A. S. K. Hashmi, I. Braun, P. Nösel, J. Schädlich, M. Wieteck, M. Rudolph, F. Rominger, Angew. Chem. 2012, 124, 4532-4536
- (2012) Angew. Chem. , vol.124 , pp. 4532-4536
- Hashmi, A.S.K.¹ Braun, I.² Nösel, P.³ Schädlich, J.⁴ Wieteck, M.⁵ Rudolph, M.⁶ Rominger, F.⁷

51
- 84860144816
- Angew. Chem. Int. Ed. 2012, 51, 4456-4460
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4456-4460

52
- 84858022319
- A. S. K. Hashmi, M. Wieteck, I. Braun, P. Nösel, L. Jongbloed, M. Rudolph, F. Rominger, Adv. Synth. Catal. 2012, 354, 555-562.
- (2012) Adv. Synth. Catal. , vol.354 , pp. 555-562
- Hashmi, A.S.K.¹ Wieteck, M.² Braun, I.³ Nösel, P.⁴ Jongbloed, L.⁵ Rudolph, M.⁶ Rominger, F.⁷

53
- 84857928276
- O. Kanno, W. Kuriyama, Z. J. Wang, F. D. Toste, Angew. Chem. 2011, 123, 10093-10096
- (2011) Angew. Chem. , vol.123 , pp. 10093-10096
- Kanno, O.¹ Kuriyama, W.² Wang, Z.J.³ Toste, F.D.⁴

54
- 80052088620
- Angew. Chem. Int. Ed. 2011, 50, 9919-9922.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9919-9922

55
- 0010218585
- 3 by 1,3-dipolar cycloaddition to form an intermediate of type 6 (Scheme2), followed by retro-1,3-cycloaddition to yield 5-phenyltetrazole with elimination of diazomethane:, P. K. Kadaba, Synlett 1990, 349-351.
- (1990) Synlett , pp. 349-351
- Kadaba, P.K.¹

56
- 84882649976
- T. J. Robilotto, N. Deligonul, J. B. Updegraff, T. G. Gray, Inorg. Chem. 2013, 52, 9659-9668; Gold(I) alkynyls react with organic azides in the presence of Cu to give gold(I) triazolyls
- (2013) Inorg. Chem. , vol.52 , pp. 9659-9668
- Robilotto, T.J.¹ Deligonul, N.² Updegraff, J.B.³ Gray, T.G.⁴

57
- 84961979591
- D. V. Partyka, L. Gao, T. S. Teets, J. B. Updegraff III, N. Deligonul, T. G. Gray, Organometallics 2009, 28, 6171-6182
- (2009) Organometallics , vol.28 , pp. 6171-6182
- Partyka, D.V.¹ Gao, L.² Teets, T.S.³ Updegraff III, J.B.⁴ Deligonu, N.⁵ Gray, T.G.⁶

58
- 84879040475
- J. E. Heckler, N. Deligonul, A. L. Rheingold, T. G. Gray, Chem. Commun. 2013, 49, 5990-5992.
- (2013) Chem. Commun. , vol.49 , pp. 5990-5992
- Heckler, J.E.¹ Deligonul, N.² Rheingold, A.L.³ Gray, T.G.⁴

59
- 0037120838
- F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12210-12216
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 12210-12216
- Himo, F.¹ Demko, Z.P.² Noodleman, L.³ Sharpless, K.B.⁴

60
- 0000262801
- Z. P. Demko, K. B. Sharpless, Angew. Chem. 2002, 114, 2214-2217
- (2002) Angew. Chem. , vol.114 , pp. 2214-2217
- Demko, Z.P.¹ Sharpless, K.B.²

61
- 0037124687
- Angew. Chem. Int. Ed. 2002, 41, 2110-2113
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2110-2113

62
- 0011089177
- Z. P. Demko, K. B. Sharpless, Angew. Chem. 2002, 114, 2217-2220
- (2002) Angew. Chem. , vol.114 , pp. 2217-2220
- Demko, Z.P.¹ Sharpless, K.B.²

63
- 0037124665
- Angew. Chem. Int. Ed. 2002, 41, 2113-2116
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2113-2116

64
- 0041519440
- F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2003, 125, 9983-9987.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 9983-9987
- Himo, F.¹ Demko, Z.P.² Noodleman, L.³ Sharpless, K.B.⁴

65
- 84875952377
- A. V. Gulevich, A. S. Dudnik, N. Chernyak, V. Gevorgyan, Chem. Rev. 2013, 113, 3084-3213.
- (2013) Chem. Rev. , vol.113 , pp. 3084-3213
- Gulevich, A.V.¹ Dudnik, A.S.² Chernyak, N.³ Gevorgyan, V.⁴

66
- 84867832041
- J. Roh, K. Vávrová, A. Hrabálek, Eur. J. Org. Chem. 2012, 6101-6118.
- (2012) Eur. J. Org. Chem. , pp. 6101-6118
- Roh, J.¹ Vávrová, K.² Hrabálek, A.³

67
- 59949090727
- L. ElKaim, L. Grimaud, Tetrahedron 2009, 65, 2153-2171
- (2009) Tetrahedron , vol.65 , pp. 2153-2171
- Elkaim, L.¹ Grimaud, L.²

68
- 84873379143
- T. Zhao, A. Boltjes, E. Herdtweck, A. Dömling, Org. Lett. 2013, 15, 639-641.
- (2013) Org. Lett. , vol.15 , pp. 639-641
- Zhao, T.¹ Boltjes, A.² Herdtweck, E.³ Dömling, A.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.