Triethylborane-induced radical reactions with gallium- and indium hydrides

Tetrahedron

Volumn 59, Issue 34, 2003, Pages 6627-6635

  Takami, Kazuaki ^a   Mikami, Satoshi ^a   Yorimitsu, Hideki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Gallium hydride; Indium hydrides; Radical mediator

Indexed keywords

ACETAL DERIVATIVE; ALUMINUM DERIVATIVE; BORANE DERIVATIVE; BROMINE DERIVATIVE; DIISOBUTYLALUMINUM HYDRIDE; GALLIUM; HALIDE; INDIUM; IODINE DERIVATIVE; REAGENT; SODIUM BIS(2 METHOXYETHOXY)ALUMINUM HYDRIDE; TRIETHYLBORANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; PRIORITY JOURNAL; RADICAL REACTION; STOICHIOMETRY;

EID: 0042703292     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01016-0     Document Type: Article

References (59)

1. (a) Neumann W.P. Synthesis. 1987;665-683
2. (b) Curran D.P., Porter N.A., Giese B. Stereochemistry of Radical Reactions. 1996;VCH, Weinheim,
3. (c) Giese B., Kopping B., Göbel T., Dickhaut J., Thoma G., Kulicke K.J., Trach F. Org. React. 48:1996;301-856.
4. Boyer I.J. Toxicology. 55:1989;253-298.
5. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
6. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
7. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
8. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
9. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
10. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
11. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
12. Studies on removal of tin residues or on tin hydride-catalized reaction in conjunction with a stoichiometric reductant: (a) Crich D., Sun S. J. Org. Chem. 61:1996;7200-7201 (b) Clive D.L.J., Yang W. J. Org. Chem. 60:1995;2607-2609 (c) Curran D.P., Chang C.-T. J. Org. Chem. 54:1989;3140-3157 (d) Curran D.P., Hadida S. J. Am. Chem. Soc. 118:1996;2531-2533 (e) Gerlach M., Jördens F., Kuhn H., Neumann W.P., Peterseim M. J. Org. Chem. 56:1991;5971-5972 (f) Hays D.S., Fu G.C. J. Org. Chem. 61:1996;4-5 (g) Corey E.J., Suggs J.W. J. Org. Chem. 40:1975;2554-2555 (h) Stork G., Sher P.M. J. Am. Chem. Soc. 108:1986;303-304.
13. Review on radical chemistry without tin: Bagulay P.A., Walton J.C. Angew. Chem., Int. Ed. Engl. 37:1998;3072-3082.
14. (a) Chatgilialoglu C. Acc. Chem. Res. 25:1992;188-194
15. (b) Chatgilialoglu C., Guerrini A., Seconi G. Synlett. 1990;219-220
16. (c) Chatgilialoglu C., Guerrini A., Lucarini M. J. Org. Chem. 57:1992;3405-3409
17. (d) Cole S.J., Kirwan J.N., Roberts B.P., Willis C.R. J. Chem. Soc., Perkin Trans. 1. 1991;103-112
18. (e) Barton D.H.R., Jang D.O., Jaszberenyi J.C. Synlett. 1991;435-438
19. (f) Barton D.H.R., Jang D.O., Jaszberenyi J.C. Tetrahedron Lett. 31:1990;4681-4684
20. (g) Lesage M., Simoes J.A.M., Griller D. J. Org. Chem. 55:1990;5413-5414
21. (h) Yamazaki O., Togo H., Matsubayashi S., Yokoyama M. Tetrahedron. 55:1999;3735-3747
22. (i) Yamazaki O., Togo H., Nogami G., Yokoyama M. Bull. Chem. Soc. Jpn. 70:1997;2519-2523.
23. (a) Pike P., Hershberger S., Hershberger J. Tetrahedron Lett. 26:1985;6289-6290
24. (b) Pike P., Hershberger S., Hershberger J. Tetrahedron. 44:1988;6295-6304
25. (c) Gupta V., Kahne D. Tetrahedron Lett. 34:1993;591-594
26. (d) Chatgilialoglu C., Ballestri M. Organometallics. 14:1995;5017-5018
27. (e) Nakamura T., Yorimitsu H., Shinokubo H., Oshima K. Synlett. 1999;1415-1416
28. (f) Nakamura T., Yorimitsu H., Shinokubo H., Oshima K. Bull. Chem. Soc. Jpn. 74:2001;747-752.
29. (a) Barton D.H.R., Jang D.O., Jaszberenyi J.C. J. Org. Chem. 58:1993;6838-6842
30. (b) Jang D.O., Song S.H. Tetrahedron Lett. 41:2000;247-249
31. (c) Yorimitsu H., Shinokubo H., Oshima K. Bull. Chem. Soc. Jpn. 74:2001;225-235. and references therein.
32. Fujita K., Nakamura T., Yorimitsu H., Oshima K. J. Am. Chem. Soc. 123:2001;3137-3138.
33. The reaction of dichlorogallane with ethyl halides has been reported, although the reaction was concluded to proceed via σ-bond metathesis: (a) Csákvári B., Jenei S., Knausz D., Meszticzky A. Acta Chim. Acad. Sci. Hung. 59:1969;225-227 (b) Meszticzky A., Knausz D., Csákvári B., Emmer J. Acta Chim. Acad. Sci. Hung. 89:1976;203-208.
34. The reaction of dichlorogallane with ethyl halides has been reported, although the reaction was concluded to proceed via σ-bond metathesis: (a) Csákvári B., Jenei S., Knausz D., Meszticzky A. Acta Chim. Acad. Sci. Hung. 59:1969;225-227 (b) Meszticzky A., Knausz D., Csákvári B., Emmer J. Acta Chim. Acad. Sci. Hung. 89:1976;203-208.
35. (a) Wiberg E., Schmidt M. Z. Naturforsch. 12b:1957;54-58
36. (b) Yamada M., Tanaka K., Araki S., Butsugan Y. Tetrahedron Lett. 36:1995;3169-3172
37. (c) Takami K., Yorimitsu H., Oshima K. Org. Lett. 4:2002;2993-2995
38. (d) Miyai T., Inoue K., Yasuda M., Shibata I., Baba A. Tetrahedron Lett. 39:1998;1929-1932
39. (e) Inoue K., Yasuda M., Shibata I., Baba A. Tetrahedron Lett. 41:2000;113-116
40. (f) Inoue K., Sawada A., Shibata I., Baba A. Tetrahedron Lett. 42:2001;4661-4663
41. (g) Inoue K., Sawada A., Shibata I., Baba A. J. Am. Chem. Soc. 124:2002;906-907
42. (h) Inoue K., Ishida T., Shibata I., Baba A. Adv. Synth. Catal. 344:2002;283-287
43. (i) Ranu B.C., Samanta S. Tetrahedron Lett. 43:2002;7405-7407.
44. 4 used for reduction of various functional groups such as carbonyl groups and halides: (a) Schmidba H., Findeiss W., Gast E. Angew. Chem., Int. Ed. Engl. 4:1965;152 (b) Choi J.H., Yun J.H., Hwang B.K., Baek D.J. Bull. Kor. Chem. Soc. 18:1997;541-542 (c) Kim J.S., Choi J.H., Kim H.D., Yun J.H., Joo C.Y., Baek D.J. Bull. Kor. Chem. Soc. 20:1999;237-240. Review on gallium hydrides: (d) Barron A.R., MacInnes A.N. King R.B. Encyclopedia of Inorganic Chemistry. Vol. 3:1994;1249 Wiley, Chichester.
45. 4 used for reduction of various functional groups such as carbonyl groups and halides: (a) Schmidba H., Findeiss W., Gast E. Angew. Chem., Int. Ed. Engl. 4:1965;152 (b) Choi J.H., Yun J.H., Hwang B.K., Baek D.J. Bull. Kor. Chem. Soc. 18:1997;541-542 (c) Kim J.S., Choi J.H., Kim H.D., Yun J.H., Joo C.Y., Baek D.J. Bull. Kor. Chem. Soc. 20:1999;237-240. Review on gallium hydrides: (d) Barron A.R., MacInnes A.N. King R.B. Encyclopedia of Inorganic Chemistry. Vol. 3:1994;1249 Wiley, Chichester.
46. 4 used for reduction of various functional groups such as carbonyl groups and halides: (a) Schmidba H., Findeiss W., Gast E. Angew. Chem., Int. Ed. Engl. 4:1965;152 (b) Choi J.H., Yun J.H., Hwang B.K., Baek D.J. Bull. Kor. Chem. Soc. 18:1997;541-542 (c) Kim J.S., Choi J.H., Kim H.D., Yun J.H., Joo C.Y., Baek D.J. Bull. Kor. Chem. Soc. 20:1999;237-240. Review on gallium hydrides: (d) Barron A.R., MacInnes A.N. King R.B. Encyclopedia of Inorganic Chemistry. Vol. 3:1994;1249 Wiley, Chichester.
47. 4 used for reduction of various functional groups such as carbonyl groups and halides: (a) Schmidba H., Findeiss W., Gast E. Angew. Chem., Int. Ed. Engl. 4:1965;152 (b) Choi J.H., Yun J.H., Hwang B.K., Baek D.J. Bull. Kor. Chem. Soc. 18:1997;541-542 (c) Kim J.S., Choi J.H., Kim H.D., Yun J.H., Joo C.Y., Baek D.J. Bull. Kor. Chem. Soc. 20:1999;237-240. Review on gallium hydrides: (d) Barron A.R., MacInnes A.N. King R.B. Encyclopedia of Inorganic Chemistry. Vol. 3:1994;1249 Wiley, Chichester.
48. The gallium species, described as a monomeric form in the present text, would exist as a certain dimeric or polymeric form: Duke B.J., Hamilton T.P., Schaefer H.F. III. Inorg. Chem. 30:1991;4225-4229. and references cited therein.
49. (a) Nozaki K., Oshima K., Utimoto K. J. Am. Chem. Soc. 109:1987;2547-2549
50. (b) Oshima K., Utimoto K. J. Synth. Org. Chem. Jpn. 47:1989;40-52
51. (c) Yorimitsu H., Oshima K. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Vol. 1:2001;Wiley-VCH, Weinheim. Chapter 1.2
52. (d) Ollivier C., Renaud P. Chem. Rev. 101:2001;3415-3434.
53. 2.
54. (a) Ueno Y., Chino K., Watanabe M., Moriya O., Okawara M. J. Am. Chem. Soc. 104:1982;5564-5566
55. (b) Stork G., Mook R. Jr., Biller S.A., Rychnovsky S.D. J. Am. Chem. Soc. 105:1983;3741-3742.
56. Gallium-centered radical anion was reported: Brand J.C., Roberts B.P. J. Chem. Soc., Chem. Commun. 1984;109-110.
57. Baba's group has reported a radical cyclization of 5a using a combination of sodium borohydride and indium trichloride, and their procedure afforded 6a in 62% yield. See Ref. 10g.
58. Only one example of a cyclization of halo acetal with indium hydride species has been reported. In that case, only 50% of cyclized product was obtained. See Ref. 10g.
59. 3 and 2.0 and 3.0 equiv. of DIBAL-H, respectively.