Silver-catalyzed hydroamination of siloxy alkynes

Angewandte Chemie - International Edition

Volumn 45, Issue 30, 2006, Pages 4991-4993

  Sun, Jianwei ^a   Kozmin, Sergey A ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Alkynes; Homogeneous catalysis; Hydroamination; Silver

Indexed keywords

BOND-FORMING STEPS; HOMOGENEOUS CATALYSIS; HYDROAMINATION; SILYLATION METHODS;

AMINATION; CATALYSIS; CHEMICAL BONDS; COMPLEXATION; REACTION KINETICS; SILVER;

OLEFINS;

ALKYNE; AMIDE; CARBAMIC ACID DERIVATIVE; ORGANOSILICON DERIVATIVE; SILVER;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; AMIDES; AMINATION; CARBAMATES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; SILVER;

EID: 33746747614     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601276     Document Type: Article

References (60)

1. For selected reviews, see: a) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703;
2. b) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105-4108;
3. Angew. Chem. Int. Ed. 2001, 40, 3983-3985;
4. c) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114;
5. d) M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. 2004, 116, 3448-3479;
6. Angew. Chem. Int. Ed. 2004, 43, 3368-3398;
7. e) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159.
8. For representative examples, see: a) W. Reppe, Justus Liebigs Ann. Chem. 1956, 601, 81-138;
9. b) M. Kimura, S. Kure, Z. Yoshida, S. Tanaka, K. Fugami, Y. Tamaru, Tetrahedron Lett. 1990, 31, 4887-4890;
10. c) P. L. McGrane, T. Livinghouse, J. Am. Chem. Soc. 1992, 114, 1323-1324;
11. d) P. J. Walsh, A. M. Baranger, R. G. Bergman, J. Am. Chem. Soc. 1992, 114, 1708-1719;
12. e) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 9295-9306;
13. f) E. M. Campi, W. R. Jackson, J. Organomet. Chem. 1996, 523, 205-209;
14. g) A. Haskel, T. Straub, M. S. Eisen, Organometallics 1996, 15, 3773-3775;
15. h) T. E. Müller, Tetrahedron Lett. 1998, 39, 5961-5962;
16. i) E. Haak, I. Bytschkov, S. Doye, Angew. Chem. 1999, 111, 3584-3586;
17. Angew. Chem. Int. Ed. 1999, 38, 3389-3391;
18. j) M. Tokunaga, M. Eckert, Y. Wakatsuki, Angew. Chem. 1999, 111, 3416-3419;
19. Angew. Chem. Int. Ed. 1999, 38, 3222-3225;
20. k) T. E. Müller, M. Grosche, E. Herdtweck, A.-P. Pleier, E. Walter, Y.-K. Yan, Organomelallics 2000, 19, 170-183;
21. l) C. G. Hartung, A. Tillack, H. Trauthwein, M. Beller, J. Org. Chem. 2001, 66, 6339-6343;
22. m) A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. 2002, 114, 2646-2648;
23. Angew. Chem. Int. Ed. 2002, 41, 2541-2544;
24. n) T. Shimada, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12670-12671;
25. o) T. Shimada, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 6646-6647;
26. p) L. L. Anderson, J. Arnold, R. G. Bergman, Org. Lett. 2004, 6, 2519-2522;
27. q) T. Shimada, G. B. Bajracharya, Y. Yamamoto, Eur. J. Org. Chem. 2005, 59-62;
28. r) L. D. Field, B. A. Messerle, K. Q. Vuong, P. Turner, Organometallics 2005, 24, 4241-4250;
29. s) A. Zulys, M. Dochnahl, D. Hollmann, K. Lohnwitz, J.-S. Herrmann, P. W. Roesky, S. Blechert, Angew. Chem. 2005, 117, 7971-7976;
30. Angew. Chem. Int. Ed. 2005, 44, 7794-7798;
31. t) L. J. Gooßen, J. E. Rauhaus, G. Deng, Angew. Chem. 2005, 117, 4110-4113;
32. Angew. Chem. Int. Ed. 2005, 44, 4042-4045.
33. For examples of intermolecular alkyne hydroamination with amides, see: T. Kondo, A. Tanaka, S. Kotachi, Y. Watanabe, J. Chem. Soc. Chem. Commun. 1995, 413-414.
34. For use of secondary amines, see: a) Y. Uchimaru, Chem. Commun. 1999, 1133-1134;
35. b) J. Barluenga, F. Aznar, R. Liz, R. Rodes, J. Chem. Soc. Perkin Trans. 1 1980, 2732-2737;
36. c) J. Barluenga, F. Aznar, Synthesis 1977, 195-197.
37. For Pd-catalyzed oxidative alkene amination with cyclic carbamates, see: V. I. Timokhin, S. S. Stahl, J. Am. Chem. Soc. 2005, 127, 17888-17893.
38. a) M. P. Schramm, D. S. Reddy, S. A. Kozmin, Angew. Chem. 2004, 116, 4404-4407;
39. Angew. Chem. Int. Ed. 2001, 40, 4274-4277;
40. b) R. F. Sweis, M. P. Schramm, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 7442-7443;
41. c) D. S. Reddy, S. A. Kozmin, J. Org. Chem. 2004, 69, 4860-4862;
42. d) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 10204-10205;
43. e) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 11806-11807;
44. f) J. Sun, S. A. Kozmin, J. Am. Chem. Soc. 2005, 127, 13512-13513.
45. For examples of Au-catalyzed hydroamination of alkynes, alkenes, and dienes, see: a) Y. Fukuda, K. Utimoto, Synthesis 1991, 975-978;
46. b) A. Arcadi, S. Di Giuseppe, F. Marinelli, E. Rossi, Adv. Synth. Catal. 2001, 343, 443-446;
47. c) E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349-3352;
48. d) J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc. 2006, 128, 1798-1799;
49. e) C. Brouwer, C. He, Angew. Chem. 2006, 118, 1776-1779;
50. Angew. Chem. Int. Ed. 2006, 45, 1744-1747;
51. f) D. Kadzimirsz, D. Hildebrandt, K. Merz, G. Dyker, Chem. Commun. 2006, 6, 661-662.
52. a) R. S. Robinson, M. C. Dovey, D. Gravestock, Eur. J. Org. Chem. 2005, 505-511;
53. b) Y. Luo, Z. Li, C. Li, Org. Lett. 2005, 7, 2675-2678; hydroamination was proposed to precede cyclization.
54. See the Supporting Information for detailed procedures.
55. For a proposed six -membered transition state in the Pd-catalyzed oxidative amination of alkenes, see: J. L. Brice, J. E. Harang, V. I. Timokhin, N. R. Anastasi, S. S. Stahl, J. Am. Chem. Soc. 2005, 127, 2868-2869.
56. For selected examples of the synthetic utility of silyl ketene acetals and aminals, see: a) I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063-2192;
57. b) Silicon in Organic, Organometallic, and Polymer Chemistry (Ed.: M. A. Brook), Wiley-VCH, Weinheim, 2000;
58. c) I. F. Lutsenko, Y. I. Baukov, A. S. Kostyuk, N. I. Savelyeva, V. K. Krysina, J. Organomet. Chem. 1969, 17, 241-262;
59. d) R. Zerrer, G. Simchen, Synthesis 1992, 922-924;
60. e) K. Neuschütz, J. Simone, T. Thyrann, R. Neier, Helv. Chim. Acta 2000, 83, 2712-2737.