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Volumn 127, Issue 10, 2005, Pages 3473-3485

Synthesis of macrocycles via cobalt-mediated [2 + 2 + 2] cycloadditions

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; IRRADIATION; REACTION KINETICS; SYRINGES; THERMAL EFFECTS; TOLUENE;

EID: 14944380049     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045001w     Document Type: Article
Times cited : (170)

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    • 4 did not meaningfully influence the macrocyclization of diyne 8 and p-tolunitrile via a template effect.
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    • and references therein
    • 15 An atmosphere of CO has been shown to regenerate the active cobalt catalyst in the Pauson-Khand reaction, see: (a) Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020 and references therein. (b) Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183-1186.
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    • 15 An atmosphere of CO has been shown to regenerate the active cobalt catalyst in the Pauson-Khand reaction, see: (a) Krafft, M. E.; Boñaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004-3020 and references therein. (b) Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183-1186.
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    • 7g
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    • 2, 0.005 M in DME, reflux, ca. 18 h) to obtain low yields of benzannulated products iia (25%) or iib (10%).
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    • (b) cod = 1.5-cyclooctadiene.
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    • Vollhardt, K. P. C.; Naiman, A. U.S. Patent 4,328,343, 1982; Chem. Abstr. 1978, 90, 186806.
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    • Vollhardt, K.P.C.1    Naiman, A.2
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    • note
    • A survey of cyanamide reactivity with diynes of varying tethered lengths in given in ref 36.
  • 102
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    • and references therein
    • Aminopyridines, which are important as pharmaceutical agents, ligands in inorganic and organometallic chemistry, and fluorescent dyes, are typically prepared by the substitution of halogenated pyridines (Thomas, S.; Roberts, S.; Pasumansky, L.; Gamsey, S.; Singaram, B. Org. Lett. 2003, 5, 3867-3870 and references therein).
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    • Thomas, S.1    Roberts, S.2    Pasumansky, L.3    Gamsey, S.4    Singaram, B.5
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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    • Earl, R.A.1    Vollhardt, K.P.C.2
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6991-6993
    • Earl, R.A.1    Vollhardt, K.P.C.2
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
    • (1977) Tetrahedron Lett. , pp. 1333-1336
    • Hong, P.1    Yamazaki, H.2
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    • (1977) Synthesis , pp. 50-52
    • Hong, P.1    Yamazaki, H.2
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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    • Hoberg, H.1    Oster, B.W.2
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
    • (1982) Synthesis , pp. 324-325
    • Hoberg, H.1    Oster, B.W.2
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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    • Bradshaw, J.S.1    Nakatsuji, Y.2    Huszthy, P.3    Wilson, B.E.4    Dalley, N.K.5    Izatt, R.M.6
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    • For cobalt-mediated cycloaddition of alkynes with isocyanates, see: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800. (b) Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991-6993. (c) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336. (d) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52. For nickel-mediated cycloaddition of alkynes with isocyanates, see: (e) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364. (f) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38. (g) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325. For the synthesis of pyridone-containing macrocycles without using transition metals, see: (h) Bradshaw, J. S.; Nakatsuji, Y.; Huszthy, P.; Wilson, B. E.; Dalley, N. K.; Izatt, R. M. J. Heterocycl. Chem. 1986, 23, 353-360. For a recent synthesis of 2-pyridones, see: (i) Hachiya, I.; Ogura, K.; Shimizu, M. Org. Lett. 2002, 4, 2755-2757.
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    • Hachiya, I.1    Ogura, K.2    Shimizu, M.3
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    • note
    • The larger amount of the Co(I) catalyst was used to achieve complete reactions. DME was found to be a better solvent than 1,4-dioxane.
  • 114
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    • note
    • 42a For example:
  • 116
    • 14944364359 scopus 로고    scopus 로고
    • note
    • 42a,b
  • 117
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    • note
    • cod = 1,5-cyclooctadiene; Cp* = pentamethylcyclopentadienide.
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    • note
    • 3.
  • 135
    • 14944363949 scopus 로고    scopus 로고
    • ref 16b
    • 2/tppts: (n) ref 16b.
  • 136
    • 14944341882 scopus 로고    scopus 로고
    • note
    • 15 See Supporting Information.
  • 137
    • 14944340897 scopus 로고    scopus 로고
    • note
    • Dimethyl 2,2-di(prop-2-ynyl)malonate and maleic anhydride gave no cycloadduct under these reaction conditions; mostly unreacted diyne was observed at the end of the reaction.
  • 141
    • 0000667768 scopus 로고    scopus 로고
    • An issue of Chem. Rev. is devoted to computational transition-metal chemistry: (a) Chem. Rev. 2000, 100, 351-818. (b) Davidson, E. R. Chem. Rev. 2000, 100, 351-352. See also ref 19.
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    • An issue of Chem. Rev. is devoted to computational transition-metal chemistry: (a) Chem. Rev. 2000, 100, 351-818. (b) Davidson, E. R. Chem. Rev. 2000, 100, 351-352. See also ref 19.
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    • Davidson, E.R.1
  • 143
    • 14944348893 scopus 로고    scopus 로고
    • note
    • 18 without the use of syringe-pump addition or high-intensity light (see equation below).
  • 144
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    • This conversion presumably occurs via a retrocyclization, rotation, and ring-closure sequence. (a) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267-5269. (b) Fritch, J. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 9-11.
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    • Ville, G.1    Vollhardt, K.P.C.2    Winter, M.J.3
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    • This conversion presumably occurs via a retrocyclization, rotation, and ring-closure sequence. (a) Ville, G.; Vollhardt, K. P. C.; Winter, M. J. J. Am. Chem. Soc. 1981, 103, 5267-5269. (b) Fritch, J. R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1979, 18, 9-11.
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  • 146
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    • note
    • See the Supporting Information for general experimental methods.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.