메뉴 건너뛰기




Volumn 16, Issue 20, 1997, Pages 4327-4345

Rhodium-catalyzed silylformylation of acetylenic bonds: Its scope and mechanistic considerations

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0000803743     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970549f     Document Type: Article
Times cited : (77)

References (158)
  • 3
    • 0000754974 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • (c) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 3, p 1015.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 1015
    • Thompson, D.J.1
  • 5
    • 85033172274 scopus 로고    scopus 로고
    • Ger. Offen. 849,548, 1938
    • (a) Roelen, O. Ger. Offen. 849,548, 1938.
    • Roelen, O.1
  • 7
    • 72749119996 scopus 로고
    • Stone, F. G. A., West, R., Eds.; Academic Press: New York
    • (c) Pruett, R. L. In Advanced Organometallic Chemistry; Stone, F. G. A., West, R., Eds.; Academic Press: New York, 1979; Vol. 17, p 1.
    • (1979) Advanced Organometallic Chemistry , vol.17 , pp. 1
    • Pruett, R.L.1
  • 9
    • 0001007350 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • (e) Stille, J. K In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, p 913.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 913
    • Stille, J.K.1
  • 70
    • 85033172339 scopus 로고    scopus 로고
    • note
    • 3CN, and THF.
  • 71
    • 85033174204 scopus 로고    scopus 로고
    • note
    • 29
  • 73
    • 85033161653 scopus 로고    scopus 로고
    • note
    • 3 solutions of the isolated E and Z isomers settled down into an identical mixture (Z:E = 19:81) even in the absence of HI, all these results consistently suggest that the E form of the silylformylation product is generally more thermodynamically stable than the Z form.
  • 74
    • 85033164754 scopus 로고    scopus 로고
    • note
    • 2SiH was in some cases complemented by the use of acetonitrile as a solvent instead of benzene (see entries 7, 8, and 11 in Table 2).
  • 78
    • 85033177544 scopus 로고    scopus 로고
    • note
    • It is difficult to determine the precise positions of substituents of 19 from NMR spectra. We carried out protodesilylation of 19 by KF in aqueous MeOH at 25 °C for 36 h to give 21 as a single product. Assignment of 21 was unequivocally performed by the comparison of spectral data with those of an authentic sample prepared according to the sequence shown: equation presented
  • 79
    • 85033179326 scopus 로고    scopus 로고
    • note
    • 16b equation presented
  • 84
    • 0001334715 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K.
    • (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, p 1037.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037
    • Schore, N.E.1
  • 90
    • 84942776708 scopus 로고
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K.
    • (a) Mackay, K. M.; Nicholson, B. K. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 6, p 1043.
    • (1982) Comprehensive Organometallic Chemistry , vol.6 , pp. 1043
    • Mackay, K.M.1    Nicholson, B.K.2
  • 91
  • 92
    • 5244363385 scopus 로고
    • Mn: (a) Berry, A. D.; MacDiarmid, A. G. Inorg. Nucl. Chem. Lett. 1969, 5, 601. (b) Gladysz, J. A.; Williams, G. M.; Tam, W.; Johnson, D. L.; Parker, D. W.; Selover, J. C. Inorg. Chem. 1979, 18, 553.
    • (1969) Inorg. Nucl. Chem. Lett. , vol.5 , pp. 601
    • Berry, A.D.1    MacDiarmid, A.G.2
  • 94
    • 33947298665 scopus 로고
    • Re: (a)Hoyano, J. K.; Elder, M.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 4568. (b) Elder, M. Inorg. Chem. 1970, 9, 762. (c) Webb, M. J.; Graham, W. A. G. J. Organomet. Chem. 1975, 93, 119. (d) Couldwell, M. C.; Simpson, J.; Robinson, W. T. J. Organomet. Chem. 1976, 107, 323. (e) Cowie, M.; Bennett, M. J. Inorg. Chem. 1977, 16, 2321. (f) Tilley, D.; Bennett, M. A.; Patmore, D. J. Inorg. Chem. 1971, 10, 2387.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 4568
    • Hoyano, J.K.1    Elder, M.2    Graham, W.A.G.3
  • 95
    • 5244337721 scopus 로고
    • Re: (a)Hoyano, J. K.; Elder, M.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 4568. (b) Elder, M. Inorg. Chem. 1970, 9, 762. (c) Webb, M. J.; Graham, W. A. G. J. Organomet. Chem. 1975, 93, 119. (d) Couldwell, M. C.; Simpson, J.; Robinson, W. T. J. Organomet. Chem. 1976, 107, 323. (e) Cowie, M.; Bennett, M. J. Inorg. Chem. 1977, 16, 2321. (f) Tilley, D.; Bennett, M. A.; Patmore, D. J. Inorg. Chem. 1971, 10, 2387.
    • (1970) Inorg. Chem. , vol.9 , pp. 762
    • Elder, M.1
  • 96
    • 0011691265 scopus 로고
    • Re: (a)Hoyano, J. K.; Elder, M.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 4568. (b) Elder, M. Inorg. Chem. 1970, 9, 762. (c) Webb, M. J.; Graham, W. A. G. J. Organomet. Chem. 1975, 93, 119. (d) Couldwell, M. C.; Simpson, J.; Robinson, W. T. J. Organomet. Chem. 1976, 107, 323. (e) Cowie, M.; Bennett, M. J. Inorg. Chem. 1977, 16, 2321. (f) Tilley, D.; Bennett, M. A.; Patmore, D. J. Inorg. Chem. 1971, 10, 2387.
    • (1975) J. Organomet. Chem. , vol.93 , pp. 119
    • Webb, M.J.1    Graham, W.A.G.2
  • 97
    • 0000882553 scopus 로고
    • Re: (a)Hoyano, J. K.; Elder, M.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 4568. (b) Elder, M. Inorg. Chem. 1970, 9, 762. (c) Webb, M. J.; Graham, W. A. G. J. Organomet. Chem. 1975, 93, 119. (d) Couldwell, M. C.; Simpson, J.; Robinson, W. T. J. Organomet. Chem. 1976, 107, 323. (e) Cowie, M.; Bennett, M. J. Inorg. Chem. 1977, 16, 2321. (f) Tilley, D.; Bennett, M. A.; Patmore, D. J. Inorg. Chem. 1971, 10, 2387.
    • (1976) J. Organomet. Chem. , vol.107 , pp. 323
    • Couldwell, M.C.1    Simpson, J.2    Robinson, W.T.3
  • 98
    • 3743142718 scopus 로고
    • Re: (a)Hoyano, J. K.; Elder, M.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 4568. (b) Elder, M. Inorg. Chem. 1970, 9, 762. (c) Webb, M. J.; Graham, W. A. G. J. Organomet. Chem. 1975, 93, 119. (d) Couldwell, M. C.; Simpson, J.; Robinson, W. T. J. Organomet. Chem. 1976, 107, 323. (e) Cowie, M.; Bennett, M. J. Inorg. Chem. 1977, 16, 2321. (f) Tilley, D.; Bennett, M. A.; Patmore, D. J. Inorg. Chem. 1971, 10, 2387.
    • (1977) Inorg. Chem. , vol.16 , pp. 2321
    • Cowie, M.1    Bennett, M.J.2
  • 99
    • 0000681489 scopus 로고
    • Re: (a)Hoyano, J. K.; Elder, M.; Graham, W. A. G. J. Am. Chem. Soc. 1969, 91, 4568. (b) Elder, M. Inorg. Chem. 1970, 9, 762. (c) Webb, M. J.; Graham, W. A. G. J. Organomet. Chem. 1975, 93, 119. (d) Couldwell, M. C.; Simpson, J.; Robinson, W. T. J. Organomet. Chem. 1976, 107, 323. (e) Cowie, M.; Bennett, M. J. Inorg. Chem. 1977, 16, 2321. (f) Tilley, D.; Bennett, M. A.; Patmore, D. J. Inorg. Chem. 1971, 10, 2387.
    • (1971) Inorg. Chem. , vol.10 , pp. 2387
    • Tilley, D.1    Bennett, M.A.2    Patmore, D.J.3
  • 100
    • 0347416258 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 3597
    • Kirch, L.1    Orehin, M.2
  • 101
    • 33947484086 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 1133
    • Harrod, J.F.1    Chalk, A.J.2
  • 102
    • 0000737369 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1640
    • Chalk, A.J.1    Harrod, J.F.2
  • 103
    • 33947299772 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1969) Inorg. Chem. , vol.8 , pp. 986
    • Baay, Y.L.1    MacDiarmid, A.G.2
  • 104
    • 33947300449 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 7051
    • Sommer, L.H.1    Lyons, J.E.2    Fujimoto, H.3
  • 105
    • 37049132908 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1974) J. Chem. Soc., Dalton Trans. , pp. 264
    • Bradley, G.F.1    Stobart, S.R.2
  • 106
    • 33847087799 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1980) Inorg. Chem. , vol.19 , pp. 3858
    • Reichel, C.L.1    Wrighton, M.S.2
  • 107
    • 0000856695 scopus 로고
    • Co: (a) Kirch, L.; Orehin, M. J. Am. Chem. Soc. 1959, 81, 3597. (b) Harrod, J. F.; Chalk, A. J. J. Am. Chem. Soc. 1965, 87, 1133. (c) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1967, 89, 1640. (d) Baay, Y. L.; MacDiarmid, A. G. Inorg. Chem. 1969, 8, 986. (e) Sommer, L. H.; Lyons, J. E.; Fujimoto, H. J. Am. Chem. Soc. 1969, 91, 7051. (f) Bradley, G. F.; Stobart, S. R. J. Chem. Soc., Dalton Trans. 1974, 264. (g) Reichel, C. L.; Wrighton, M. S. Inorg. Chem. 1980, 19, 3858. (h) Sisak, A.; Ungváry, F.; Markó, L. Organometallics 1986, 5, 1019.
    • (1986) Organometallics , vol.5 , pp. 1019
    • Sisak, A.1    Ungváry, F.2    Markó, L.3
  • 108
    • 0000829913 scopus 로고
    • Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K.
    • (a) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1989; Vol. 2, p 1479.
    • (1989) The Chemistry of Organic Silicon Compounds , vol.2 , pp. 1479
    • Ojima, I.1
  • 110
    • 0000487195 scopus 로고
    • Trost, B. M., Fleming, L, Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K.
    • (c) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, p 763.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 763
    • Hiyama, T.1    Kusumoto, T.2
  • 114
    • 0001587776 scopus 로고
    • (c) Onopchenko, A.; Sabourin, E. T.; Beach, D. L. J. Org. Chem. 1983, 48, 5101; 1984, 49, 3389.
    • (1984) J. Org. Chem. , vol.49 , pp. 3389
  • 127
    • 85033172549 scopus 로고    scopus 로고
    • note
    • The time required for the equilibrium in these controlled experiments was far longer than the silylformylation. Phenylacetylene may act as a catalyst for the exchange between silyl groups.
  • 128
  • 140
    • 85033158819 scopus 로고    scopus 로고
    • note
    • 1H NMR integration of the residual proton signals at the site of labeling relative to the intensity of another signal assigned to one proton at an unlabeled position.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.