Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 3999-4007

  Kawamoto, Takuji ^a   Uehara, Shohei ^a   Hirao, Hidefumi ^a   Fukuyama, Takahide ^a   Matsubara, Hiroshi ^a   Ryu, Ilhyong ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBONYLATION; RATE CONSTANTS;

CARBON-IODINE BONDS; ELECTRON DEFICIENT OLEFINS; HYDROGEN ABSTRACTION; KINETIC COMPETITIONS; RADICAL ADDITION REACTIONS; RADICAL CARBONYLATION; THREE COMPONENT REACTIONS; TRIBUTYLTIN HYDRIDE;

CARBON;

ALKENE; BORANE DERIVATIVE; BROMINE; CARBON; CHLORINE; HYDROGEN; IODIDE; ORGANIC COMPOUND; RADICAL; REAGENT; TETRABUTYLAMMONIUM; TIN; TRIBUTYLTIN; FREE RADICAL; IODINATED HYDROCARBON; SODIUM CYANOBOROHYDRIDE;

ADDITION REACTION; ARTICLE; CARBONYLATION; CONTROLLED STUDY; CROSS COUPLING REACTION; ELECTRON; RADICAL REACTION; REACTION OPTIMIZATION; REDUCTION; TEMPERATURE; CHEMICAL STRUCTURE; CHEMISTRY;

ALKENES; BOROHYDRIDES; ELECTRONS; FREE RADICALS; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE;

EID: 84899847746     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500464q     Document Type: Article

References (64)

1. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001.
2. For a review of tin-free reductive radical reactions, see: Studer, A.; Amrein, S. Synthesis 2002, 835-849
3. Barltrop, J. A.; Bradbury, D. J. Am. Chem. Soc. 1973, 95, 5085-5086
4. Groves, J. T.; Ma, K. W. J. Am. Chem. Soc. 1974, 96, 6527-6529
5. Groves, J. T.; Kittisopikul, S. Tetrahedron Lett. 1977, 18, 4291-4294
6. Abeywickrema, A. N.; Beckwith, A. L. J. Tetrahedron Lett. 1986, 27, 109-112
7. Kropp, M.; Schuster, G. B. Tetrahedron Lett. 1987, 28, 5295-5298
8. Liu, Q.; Han, B.; Zhang, W.; Yang, L.; Liu, Z.-L.; Yu, W. Synlett 2005, 2248-2250
9. Baban, J. A.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1988, 1195-1200
10. Barton, D. H. R.; Jacob, M. Tetrahedron Lett. 1998, 39, 1331-1334
11. Abe, M.; Hayashikoshi, T.; Kurata, T. Chem. Lett. 1994, 23, 1789-1792
12. Kurata, T.; Kinoshita, R. J. Oleo Sci. 2001, 50, 759-762
13. Ryu, I.; Uehara, S.; Hirao, H.; Fukuyama, T. Org. Lett. 2008, 10, 1005-1008
14. Fukuyama, T.; Kawamoto, T.; Kobayashi, M.; Ryu, I. Beilstein J. Org. Chem. 2013, 9, 1791-1796
15. Burke, S. D.; Fobare, W. F.; Armistead, D. M. J. Org. Chem. 1982, 47, 3348-3350
16. Giese, B.; Dupuis, J. Angew. Chem., Int. Ed. 1983, 22, 622-623
17. Giese, B.; González-Gómez, J. A.; Witzel, T. Angew. Chem., Int. Ed. 1984, 23, 69-70
18. Curran, D. P.; Hadida, S.; Kim, S.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 6607-6615
19. Suzuki, A.; Arase, A.; Matsumoto, H.; Itoh, M.; Brown, H. C.; Rogic, M. M.; Rathke, M. W. J. Am. Chem. Soc. 1967, 89, 5708-5709
20. Polykarpov, A. Y.; Neckers, D. C. Tetrahedron Lett. 1995, 36, 5483-5486
21. Ollivier, C.; Renaud, P. Chem. Eur. J. 1999, 5, 1468-1473
22. Ollivier, C.; Renaud, P. Angew. Chem., Int. Ed. 2000, 39, 925-928
23. Kobayashi, S.; Kawamoto, T.; Uehara, S.; Fukuyama, T.; Ryu, I. Org. Lett. 2010, 12, 1548-1551
24. Kawamoto, T.; Fukuyama, T.; Ryu, I. J. Am. Chem. Soc. 2012, 134, 875-877
25. Curran, D. P.; Solovyev, A.; Makhlouf Brahmi, M.; Fensterbank, L.; Malacria, M.; Lacôte, E. Angew. Chem., Int. Ed. 2011, 50, 10294-10317
26. Kawamoto, T.; Okada, T.; Curran, D. P.; Ryu, I. Org. Lett. 2013, 15, 2144-2147
27. Pan, X.; Lalevée, J.; Lacôte, E.; Curran, D. P. Adv. Synth. Catal. 2013, 355, 3522-3526
28. Spiegel, D. A.; Wiberg, K. B.; Schacherer, L. N.; Medeiros, M. R.; Wood, J. L. J. Am. Chem. Soc. 2005, 127, 12513-12515
29. Pozzi, D.; Scanlan, E. M.; Renaud, P. J. Am. Chem. Soc. 2005, 127, 14204-14205
30. Villa, G.; Povie, G.; Renaud, P. J. Am. Chem. Soc. 2011, 133, 5913-5920
31. Povie, G.; Marzorati, M.; Bigler, P.; Renaud, P. J. Org. Chem. 2013, 78, 1553-1558
32. -1 at 20 °C: Beuermann, S.; Buback, M. Prog. Polym. Sci. 2002, 27, 191-254
33. Newcomb, M.; Kaplan, J. Tetrahedron Lett. 1987, 28, 1615-1618
34. Newcomb, M. Tetrahedron 1993, 49, 1151-1176
35. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739-7742
36. Chatgilialoglu, C.; Dickhaut, J.; Giese, B. J. Org. Chem. 1991, 56, 6399-6403
37. Lusztyk, J.; Maillard, B.; Lindsay, D. A.; Ingold, K. U. J. Am. Chem. Soc. 1983, 105, 3578-3580
38. Solovyev, A.; Ueng, S.-H.; Monot, J.; Fensterbank, L.; Malacria, M.; Lacôte, E.; Curran, D. P. Org. Lett. 2010, 12, 2998-3001
39. Sim, T. B.; Choi, J.; Joung, M. J.; Yoon, N. M. J. Org. Chem. 1997, 62, 2357-2361
40. Van Arnum, S. D.; Moffet, H.; Carpenter, B. K. Org. Process Res. Dev. 2004, 8, 769-776
41. Maillard, B.; Forrest, D.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7024-7026
42. Newcomb, M.; Glenn, A. G. J. Am. Chem. Soc. 1989, 111, 275-277
43. Hollis, R.; Hughes, L.; Bowry, V. W.; Ingold, K. U. J. Org. Chem. 1992, 57, 4284-4287
44. Ryu, I.; Kusano, K.; Yamazaki, H.; Sonoda, N. J. Org. Chem. 1991, 56, 5003-5005
45. Ryu, I.; Hasegawa, M.; Kurihara, A.; Ogawa, A.; Tsunoi, S.; Sonoda, N. Synlett 1993, 143-145
46. Kishimoto, Y.; Ikariya, T. J. Org. Chem. 2000, 65, 7656-7659
47. Corey, E. J.; Suggs, J. W. J. Org. Chem. 1975, 40, 2554-2555
48. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304
49. -1 at 0 °C in MeCN: Caronna, T.; Citterio, A.; Ghirardini, M.; Minisci, F. Tetrahedron 1977, 33, 793-796
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
51. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25-35
52. Pan, X.; Lacôte, E.; Lalevée, J.; Curran, D. P. J. Am. Chem. Soc. 2012, 134, 5669-5674
53. Giles, J. R. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1983, 743-755
54. Sheeller, B.; Ingold, K. U. J. Chem. Soc., Perkin Trans. 2 2001, 480-486
55. Barrett, A. G. M.; Tam, W. J. Org. Chem. 1997, 62, 7673-7678
56. Shukla, P.; Hsu, Y.-C.; Cheng, C.-H. J. Org. Chem. 2006, 71, 655-658
57. Yamazaki, O.; Togo, H.; Matubayashi, S.; Yokoyama, M. Tetrahedron 1999, 55, 3735-3747
58. Paolobelli, A. B.; Ruzziconi, R. J. Org. Chem. 1996, 61, 6434-6437
59. Blay, G.; Cardona, L.; Garcia, B.; Lahoz, L.; Pedro, J. Tetrahedron 1996, 52, 8611-8618
60. Zhang, D.; Ready, J. M. Org. Lett. 2005, 7, 5681-5683
61. Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12670-12671
62. Rieke, R. D.; Klein, W. R.; Wu, T.-C. J. Org. Chem. 1993, 58, 2492-2500
63. Cai, Y.; Roberts, B. P.; Tocher, D. A.; Barnett, S. A. Org. Biomol. Chem. 2004, 2, 2517-2529
64. Lu, X.; Ji, J.; Ma, D.; Shen, W. J. Org. Chem. 1991, 56, 5774-5778