Iron-Induced regio- and stereoselective addition of sulfenyl chlorides to alkynes by a radical pathway

Angewandte Chemie - International Edition

Volumn 53, Issue 50, 2014, Pages 13880-13884

  Iwasaki, Masayuki ^a   Fujii, Tomoya ^a   Nakajima, Kiyohiko ^b   Nishihara, Yasushi ^a,c  

^a OKAYAMA UNIVERSITY   (Japan)

^b AICHI UNIVERSITY OF EDUCATION   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Alkynes; Chlorothiolation; Iron; Radical reactions; Synthetic methods

Indexed keywords

CHELATION; CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; IRON; IRON COMPOUNDS; REACTION KINETICS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ALKYNES; CHLOROTHIOLATION; CROSS COUPLING REACTIONS; RADICAL REACTIONS; STEREOSELECTIVE ADDITION; SULFUR-CENTERED RADICALS; SYNTHETIC METHODS; TRANSITION-METAL-CATALYZED REACTIONS;

HYDROCARBONS;

EID: 84918797378     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201408121     Document Type: Article

References (72)

1. a) I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435-3461
2. b) L.-B. Han, M. Tanaka, Chem. Commun. 1999, 395-402
3. c) I. Beletskaya, C. Moberg, Chem. Rev. 2006, 106, 2320-2354.
4. I.P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596-1636.
5. a) E. Marcantoni, M. Massaccesi, M. Petrini, G. Bartoli, M. C. Bellucci, M. Bosco, L. Sambri, J. Org. Chem. 2000, 65, 4553-4559
6. b) H. S. Sader, D. M. Johnson, R. N. Jones, Antimicrob. Agents Chemother. 2004, 48, 53-62.
7. a) T. Ishiyama, K. Nishijima, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 7219-7225
8. b) H. Kuniyasu, A. Ogawa, S. Miyazaki, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1991, 113, 9796-9803
9. c) Y. Gareau, A. Orellana, Synlett 1997, 803-804
10. d) M. Arisawa, M. Yamaguchi, Org. Lett. 2001, 3, 763-764
11. e) Y Gareau, M. Tremblay, D. Gauvreau, H. Juteau, Tetrahedron 2001, 57, 5739-5750
12. f) V. P. Ananikov, M. A. Kabeshov, I.P Beletskaya, G G Aleksandrov, I. L. Eremenko, J. Organomet. Chem. 2003, 687, 451-461
13. g) M. Arisawa, Y Kozuki, M. Yamaguchi, J. Org. Chem. 2003, 68, 8964-8967
14. h) V. P. Anani kov, K. A. Gayduk, I. P. Beletskaya, V. N. Khrustalev, M. Y Antipin, Chem. Eur. J. 2008, 14, 2420-2434
15. i) V. P. Ananikov, K. A. Gayduk, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev, M. Y Antipin, Chem. Eur. J. 2010, 16, 2063-2071
16. j) L.-B. Han, M. Tanaka, J. Am. Chem. Soc. 1998, 120, 8249-8250
17. k) L.-B. Han, M. Tanaka, Chem. Lett. 1999, 863-864
18. l) N. Hoshi, T Kashiwabara, M. Tanaka, Tetrahedron Lett. 2012, 53, 2078-2081.
19. a) A. Ogawa, J. Synth. Org. Chem. Jpn. 1995, 53, 869-880
20. b) A. Ogawa, T Hirao, Rev. Heteroat. Chem. 1998, 18, 1-10
21. c) P. Renurd, Top. Curr. Chem. 2000, 208, 81-112
22. d) H. Yorimitsu, Beilstein J. Org. Chem. 2013, 9, 1269-1277
23. e) U. Wille, Chem. Rev. 2013, 113, 813-853
24. f) S. Kawaguchi, A. Ogawa, Synlett 2013, 2199-2215.
25. a) R. C. Fuson, C. C. Price, R. A. Bauman, O. H. Bullitt, Jr., W. R. Hatchard, E. W. Maynert, J. Org. Chem. 1946, 11, 469-474
26. b) W. E. Truce, H. E. Hill, M. M. Boudakian, J. Am. Chem. Soc. 1956, 78, 2760-2762
27. c) V. Caló, G. Scorrano, G. Modena, J. Org. Chem. 1969, 34, 2020-2022
28. d) G H. Schmid, A. Modro, D. G Garratt, K. Yates, Can. J. Chem. 1976, 54, 3045-3049
29. e) G H. Schmid, A. Modro, F Lenz, D. G. Garratt, K. Yates, J. Org. Chem. 1976, 41, 2331-2336
30. f) G. Capozzi, C. Caristi, V. Lucchini, G. Modena, J. Chem. Soc. Perkin Trans. 11982, 2197-2201
31. g) G. Capozzi, G. Romeo, V. Lucchini, G. Modena, J. Chem. Soc. Perkin Trans. 11983, 831-835
32. h) L. Zhong, P. R. Savoie, A. S. Filatov, J. T. Welch, Angew. Chem. Int. Ed. 2014, 53, 526-529
33. Angew. Chem. 2014, 126, 536-539
34. i) L. Benati, P. C. Montevecchi, P. Spagnolo, Tetrahedron 1993, 49, 5365-5376.
35. a) W. E. Truce, G. C. Wolf, J. Org. Chem. 1971, 36, 1727-1732
36. b) Y. Amiel, J. Org. Chem. 1971, 36, 3691-3696
37. c) Y. Amiel, J. Org. Chem. 1971, 36, 3697-3702
38. d) Y. Amiel, Tetrahedron Lett. 1971, 12, 661-663
39. e) Y. Amiel, J. Org. Chem. 1974, 39, 3867-3870
40. f) X. Liu, X. Duan, Z. Pan, Y. Han, Y. Liang, Synlett 2005, 1752-1754
41. g) X. Zeng, L. Ilies, E. Nakamura, Org. Lett. 2012, 14, 954-956
42. h) C. Chen, J. Su, X. Tong, Chem. Eur. J. 2013, 19, 5014-5018
43. i) X. Li, X. Shi, M. Fang, X. Xu, J. Org. Chem. 2013, 78, 9499-9504.
44. M. Iwasaki, T, Fujii, A. Yamamoto, K. Nakajima, Y Nishihara, Chem. Asian J. 2014, 9, 58-62.
45. a) L. L. Hegedus, R. W McCabe, Catalyst Poisoning, Marcel Dekker, New York, 1984
46. b) A. T Hutton in Comprehensive Coordination Chemistry, Vol. 5 (Eds.: G Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon, Oxford, 1984.
47. a) B. Jiang, H. Tian, Z.-G Huang, M. Xu, Org. Lett. 2008, 10, 2737-2740
48. b) M. J. Bodner, R. M. Phelan, C A. Townsend, Org. Lett. 2009, 11, 3606-3609.
49. CCDC-1018081 (7) and 1018083 (13) 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.
50. Y Hou, I. A. Abu-Yousef, D N. Harpp, Tetrahedron Lett. 2000, 41, 7809-7812.
51. a) N. Taniguchi, Tetrahedron 2009, 65, 2782-2790
52. a) A. G Larsen, A. H. Holm, M. Roberson, K. Daasbjerg, J. Am. Chem. Soc. 2001, 123, 1723-1729
53. b) C. Ji, M. Ahmida, M. Chahma, A. Houmam, J. Am. Chem. Soc. 2006, 128, 15423-15431.
54. R. W Fessenden, R. H. Schuler, J. Chem. Phys. 1963, 39, 2147-2195.
55. D P. Curran, N. A. Porter, B. Giese, Stereochemistry of Radical Reactions, VCH Publishers, New York, 1995, chap. 6.3.
56. O. Ito, M. D. C. M. Fleming, J. Chem. Soc. Perkin Trans. 2 1989, 689-693.
57. L. A. Singer, J. Chen, Tetrahedron Lett. 1969, 10, 4849-4854.
58. O. Simamura, K. Tokumaru, H. Yui, Tetrahedron Lett. 1966, 7, 5141-5144.
59. A. Miller, M. Moore, Tetrahedron Lett. 1980, 21, 577-580
60. H. Zhou, C. Zeng, L. Ren, W. Liao, X. Huang, Synlett 2006, 3504-3506
61. c) G R. Cook, R. Hayashi, Org. Lett. 2006, 8, 1045-1048
62. d) Z. Liu, J. Wang, Y Zhao, B. Zhou, Adv. Synth. Catal. 2009, 351, 371-374.
63. R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461-1473.
64. M. Alami, B. Crousse, F Ferri, J. Organomet. Chem. 2001, 624, 114-123.
65. J. Shi, E. Negishi, J. Organomet. Chem. 2003, 687, 518-524.
66. M. Mellah, A. Voituriez, E. Schulz, Chem. Rev. 2007, 107, 5133-5209.
67. C. Pettinari, M. Pellei, G Cavicchio, M. Crucianelli, W Panzeri, M. Colapietro, A. Cassetta, Organometallics 1999, 18, 555-563.
68. a) D. J. Covell, M. C. White, Tetrahedron 2013, 69, 7771-7778
69. b) J. H. Delcamp, P. E. Gorminsky, M. C. White, J. Am. Chem. Soc. 2013, 135, 8460-8463
70. c) I.I. Strambeanu, M. C. White, J. Am. Chem. Soc. 2013, 135, 12032-12037
71. d) J. H. Howell, W Lei, A. J. Young, M. C White, J. Am. Chem. Soc. 2014, 136, 5750-5754
72. e) T. J. Osberger, M. C White, J. Am. Chem. Soc. 2014, 136, 11176.