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Volumn 1996, Issue 4, 1996, Pages 377-379

Radical Reactions in Organoboron Chemistry. III - Addition Reactions to Alkynylboranes as Efficient Routes to New Regio- and Stereodefined Alkenyl Diamino- and Dialkoxyboranes

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EID: 0003115131     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5410     Document Type: Article
Times cited : (42)

References (70)
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    • Corriu, R.J.P.1    Bolin, G.2    Moreau, J.J.E.3
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    • (1994) J. Org. Chem. , vol.59 , pp. 8178
    • Nakamura, E.1    Imanishi, Y.2    Machii, D.3
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    • For reviews, see : Motherwell, W.B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Katritzky, A.R., Meth-Cohn, O.; Rees, C.W. Eds, Academic Press, New York, 1992. Curran, D.P. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming, I. Eds, Pergamon Press, Oxford, 1991, vol. 4, 770. For some recent references on intermolecular radical additions to alkynes, see : Hydrostannation : Oshima, K. Advances in Metal-Organic Chemistry 1991, 2, 101. Crisp, G.T.; Glink, P.T. Tetrahedron Lett. 1992, 33, 4649. Corriu, R.J.P.; Bolin, G.; Moreau, J.J.E. Bull. Soc. Chim. Fr. 1993, 130, 273, Nakamura, E.; Imanishi, Y.; Machii, D. J. Org. Chem. 1994, 59, 8178. Sulfur-centered radicals : Benati, L.; Capella, L.; Montevecchi, P.C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818. Burke, S.D.; Jung, K.W.; Perri, R.E. Tetrahedron Lett. 1994, 34, 5841. Demchuk, D.V.; Lazareva, M.I.; Lindeman, S.V.; Khrustalyov, V.N.; Struchkov, Y.T.; Ismagilov, R.F.; Troyansky, E.I.; Nikishin, G.I. Synthesis 1995, 307. Silanes : Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1993, 66, 2356. Carbon-centered radicals : Ichinose, Y.; Matsunaga, S.I.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155. Curran, D.P.; Kim, D. Tetrahedron 1991, 47, 6171. Curran, D.P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189. Mahadevan, A.; Fuchs, P.L. J. Am. Chem. Soc. 1995, 117, 3272. Balczewski, P.; Mikolajczyk, M. Synthesis 1995, 392. Perfluoroalkyl radicals : Rong, G.; Keese, R. Tetrahedron Lett. 1990, 31, 5615. Habibi, M.H.; Mallouk, T.E. J. Fluorine Chem. 1991, 55, 53. Phosphorus-centered radicals : Brumwell, J.E.; Simpkins, N.S.; Terrett, N.K. Tetrahedron Lett. 1993, 34, 1215. Heesche-Wagner, K.; Mitchell, T. J. Organomet. Chem. 1994, 468, 99.
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    • Benati, L.1    Capella, L.2    Montevecchi, P.C.3    Spagnolo, P.4
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    • For reviews, see : Motherwell, W.B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Katritzky, A.R., Meth-Cohn, O.; Rees, C.W. Eds, Academic Press, New York, 1992. Curran, D.P. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming, I. Eds, Pergamon Press, Oxford, 1991, vol. 4, 770. For some recent references on intermolecular radical additions to alkynes, see : Hydrostannation : Oshima, K. Advances in Metal-Organic Chemistry 1991, 2, 101. Crisp, G.T.; Glink, P.T. Tetrahedron Lett. 1992, 33, 4649. Corriu, R.J.P.; Bolin, G.; Moreau, J.J.E. Bull. Soc. Chim. Fr. 1993, 130, 273, Nakamura, E.; Imanishi, Y.; Machii, D. J. Org. Chem. 1994, 59, 8178. Sulfur-centered radicals : Benati, L.; Capella, L.; Montevecchi, P.C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818. Burke, S.D.; Jung, K.W.; Perri, R.E. Tetrahedron Lett. 1994, 34, 5841. Demchuk, D.V.; Lazareva, M.I.; Lindeman, S.V.; Khrustalyov, V.N.; Struchkov, Y.T.; Ismagilov, R.F.; Troyansky, E.I.; Nikishin, G.I. Synthesis 1995, 307. Silanes : Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1993, 66, 2356. Carbon-centered radicals : Ichinose, Y.; Matsunaga, S.I.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155. Curran, D.P.; Kim, D. Tetrahedron 1991, 47, 6171. Curran, D.P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189. Mahadevan, A.; Fuchs, P.L. J. Am. Chem. Soc. 1995, 117, 3272. Balczewski, P.; Mikolajczyk, M. Synthesis 1995, 392. Perfluoroalkyl radicals : Rong, G.; Keese, R. Tetrahedron Lett. 1990, 31, 5615. Habibi, M.H.; Mallouk, T.E. J. Fluorine Chem. 1991, 55, 53. Phosphorus-centered radicals : Brumwell, J.E.; Simpkins, N.S.; Terrett, N.K. Tetrahedron Lett. 1993, 34, 1215. Heesche-Wagner, K.; Mitchell, T. J. Organomet. Chem. 1994, 468, 99.
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    • Burke, S.D.1    Jung, K.W.2    Perri, R.E.3
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    • For reviews, see : Motherwell, W.B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Katritzky, A.R., Meth-Cohn, O.; Rees, C.W. Eds, Academic Press, New York, 1992. Curran, D.P. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming, I. Eds, Pergamon Press, Oxford, 1991, vol. 4, 770. For some recent references on intermolecular radical additions to alkynes, see : Hydrostannation : Oshima, K. Advances in Metal-Organic Chemistry 1991, 2, 101. Crisp, G.T.; Glink, P.T. Tetrahedron Lett. 1992, 33, 4649. Corriu, R.J.P.; Bolin, G.; Moreau, J.J.E. Bull. Soc. Chim. Fr. 1993, 130, 273, Nakamura, E.; Imanishi, Y.; Machii, D. J. Org. Chem. 1994, 59, 8178. Sulfur-centered radicals : Benati, L.; Capella, L.; Montevecchi, P.C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818. Burke, S.D.; Jung, K.W.; Perri, R.E. Tetrahedron Lett. 1994, 34, 5841. Demchuk, D.V.; Lazareva, M.I.; Lindeman, S.V.; Khrustalyov, V.N.; Struchkov, Y.T.; Ismagilov, R.F.; Troyansky, E.I.; Nikishin, G.I. Synthesis 1995, 307. Silanes : Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1993, 66, 2356. Carbon-centered radicals : Ichinose, Y.; Matsunaga, S.I.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155. Curran, D.P.; Kim, D. Tetrahedron 1991, 47, 6171. Curran, D.P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189. Mahadevan, A.; Fuchs, P.L. J. Am. Chem. Soc. 1995, 117, 3272. Balczewski, P.; Mikolajczyk, M. Synthesis 1995, 392. Perfluoroalkyl radicals : Rong, G.; Keese, R. Tetrahedron Lett. 1990, 31, 5615. Habibi, M.H.; Mallouk, T.E. J. Fluorine Chem. 1991, 55, 53. Phosphorus-centered radicals : Brumwell, J.E.; Simpkins, N.S.; Terrett, N.K. Tetrahedron Lett. 1993, 34, 1215. Heesche-Wagner, K.; Mitchell, T. J. Organomet. Chem. 1994, 468, 99.
    • (1995) Synthesis , pp. 307
    • Demchuk, D.V.1    Lazareva, M.I.2    Lindeman, S.V.3    Khrustalyov, V.N.4    Struchkov, Y.T.5    Ismagilov, R.F.6    Troyansky, E.I.7    Nikishin, G.I.8
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    • For reviews, see : Motherwell, W.B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Katritzky, A.R., Meth-Cohn, O.; Rees, C.W. Eds, Academic Press, New York, 1992. Curran, D.P. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming, I. Eds, Pergamon Press, Oxford, 1991, vol. 4, 770. For some recent references on intermolecular radical additions to alkynes, see : Hydrostannation : Oshima, K. Advances in Metal-Organic Chemistry 1991, 2, 101. Crisp, G.T.; Glink, P.T. Tetrahedron Lett. 1992, 33, 4649. Corriu, R.J.P.; Bolin, G.; Moreau, J.J.E. Bull. Soc. Chim. Fr. 1993, 130, 273, Nakamura, E.; Imanishi, Y.; Machii, D. J. Org. Chem. 1994, 59, 8178. Sulfur-centered radicals : Benati, L.; Capella, L.; Montevecchi, P.C.; Spagnolo, P. J. Org. Chem. 1994, 59, 2818. Burke, S.D.; Jung, K.W.; Perri, R.E. Tetrahedron Lett. 1994, 34, 5841. Demchuk, D.V.; Lazareva, M.I.; Lindeman, S.V.; Khrustalyov, V.N.; Struchkov, Y.T.; Ismagilov, R.F.; Troyansky, E.I.; Nikishin, G.I. Synthesis 1995, 307. Silanes : Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1993, 66, 2356. Carbon-centered radicals : Ichinose, Y.; Matsunaga, S.I.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155. Curran, D.P.; Kim, D. Tetrahedron 1991, 47, 6171. Curran, D.P.; Kim, D.; Ziegler, C. Tetrahedron 1991, 47, 6189. Mahadevan, A.; Fuchs, P.L. J. Am. Chem. Soc. 1995, 117, 3272. Balczewski, P.; Mikolajczyk, M. Synthesis 1995, 392. Perfluoroalkyl radicals : Rong, G.; Keese, R. Tetrahedron Lett. 1990, 31, 5615. Habibi, M.H.; Mallouk, T.E. J. Fluorine Chem. 1991, 55, 53. Phosphorus-centered radicals : Brumwell, J.E.; Simpkins, N.S.; Terrett, N.K. Tetrahedron Lett. 1993, 34, 1215. Heesche-Wagner, K.; Mitchell, T. J. Organomet. Chem. 1994, 468, 99.
    • (1993) Bull. Chem. Soc. Jpn. , vol.66 , pp. 2356
    • Miura, K.1    Oshima, K.2    Utimoto, K.3
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