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Volumn 129, Issue 4, 2007, Pages 790-793

Stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING; ELECTROPHILES; HETEROARYL IODIDES; ROOM TEMPERATURE;

EID: 33846570081     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064948q     Document Type: Article
Times cited : (51)

References (34)
  • 1
    • 14344266665 scopus 로고    scopus 로고
    • Review:, 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH Verlag GmbH & Co, Weinheim, Chapter 3
    • Review: Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, 2004; Vol. 1, Chapter 3.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1
    • Mitchell, T.N.1
  • 2
    • 33644942388 scopus 로고    scopus 로고
    • Recent applications in natural products total synthesis: (a) Nicolaou, K. C.; Koftis, T. V.; Vyskocil, S.; Petrovic, G.; Tang, W.; Frederick, M. O.; Chen, D. Y.-K.; Li, Y.; Ling, T.; Yamada, Y. M. A. J. Am. Chem. Soc. 2006, 128, 2859-2872.
    • Recent applications in natural products total synthesis: (a) Nicolaou, K. C.; Koftis, T. V.; Vyskocil, S.; Petrovic, G.; Tang, W.; Frederick, M. O.; Chen, D. Y.-K.; Li, Y.; Ling, T.; Yamada, Y. M. A. J. Am. Chem. Soc. 2006, 128, 2859-2872.
  • 13
    • 33748989516 scopus 로고    scopus 로고
    • Recent examples of alternative chiral allylic alcohol syntheses: (a) Berkessel, A.; Roland, K.; Neudoerfl, J. M. Org. Lett. 2006, 8, 4195-4198.
    • Recent examples of alternative chiral allylic alcohol syntheses: (a) Berkessel, A.; Roland, K.; Neudoerfl, J. M. Org. Lett. 2006, 8, 4195-4198.
  • 16
    • 33746403241 scopus 로고    scopus 로고
    • Recent examples of alternative chiral benzylic alcohol syntheses: (a) Yang, S.-D.; Shi, Y.; Sun, Z.-H.; Zhao, Y.-B.; Liang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 1895-1900.
    • Recent examples of alternative chiral benzylic alcohol syntheses: (a) Yang, S.-D.; Shi, Y.; Sun, Z.-H.; Zhao, Y.-B.; Liang, Y.-M. Tetrahedron: Asymmetry 2006, 17, 1895-1900.
  • 19
    • 33846610632 scopus 로고    scopus 로고
    • Since CuTC is used in stoichiometric amounts and apparently consumed to some extent, a reviewer suggested the term promoter instead of catalyst
    • Since CuTC is used in stoichiometric amounts and apparently consumed to some extent, a reviewer suggested the term promoter instead of catalyst.
  • 20
    • 33846582006 scopus 로고    scopus 로고
    • Catalysis or promotion ot the Stille reaction by copper salts in combination with other transition metals or alone is well established: (a) Liebeskind. L. S, Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364
    • Catalysis or promotion ot the Stille reaction by copper salts in combination with other transition metals or alone is well established: (a) Liebeskind. L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364.
  • 24
    • 0000404899 scopus 로고    scopus 로고
    • Transmetalation of organostannanes with higher order cuprates is also known: Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Am. Chem. Soc. 1988, 110, 2641-2643.
    • Transmetalation of organostannanes with higher order cuprates is also known: Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Am. Chem. Soc. 1988, 110, 2641-2643.
  • 25
    • 33846632411 scopus 로고    scopus 로고
    • We speculate that CuTC is more effective than other copper salts because it is bidentate and can establish a highly coordinated intermediate, e.g, i, that resists β-elimination. This may explain, in part, why simple aryl iodides and 1-iodocyclohexene are satisfactory coupling partners, in contrast to the experience of Allred and Liebeskind see ref. 15, Diagram presented
    • We speculate that CuTC is more effective than other copper salts because it is bidentate and can establish a highly coordinated intermediate, e.g., i, that resists β-elimination. This may explain, in part, why simple aryl iodides and 1-iodocyclohexene are satisfactory coupling partners, in contrast to the experience of Allred and Liebeskind (see ref. 15). (Diagram presented)
  • 26
    • 0029979566 scopus 로고    scopus 로고
    • The Liebeskind laboratory developed CuTC and adroitly exploited it for the cross-coupling of organostannanes with aryl and alkenyl iodides: Allred, G. D, Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749
    • The Liebeskind laboratory developed CuTC and adroitly exploited it for the cross-coupling of organostannanes with aryl and alkenyl iodides: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
  • 27
    • 33846604288 scopus 로고    scopus 로고
    • Little, if any, tri-n-butylstannyl iodide or distannane is observed in the crude product at the end of the reaction. In light of the report by Allred and Liebeskind (ref. 15) that tri-n-butylstannyl thiophene-2-carboxylate is produced in their reactions, we speculate that the tri-n-butylstannyl byproduct is sequestered in this form. It would follow, therefore, that stoichiometric amounts of CuTC would be required, and this is what we found empirically to achieve maximum yields.
    • Little, if any, tri-n-butylstannyl iodide or distannane is observed in the crude product at the end of the reaction. In light of the report by Allred and Liebeskind (ref. 15) that tri-n-butylstannyl thiophene-2-carboxylate is produced in their reactions, we speculate that the tri-n-butylstannyl byproduct is sequestered in this form. It would follow, therefore, that stoichiometric amounts of CuTC would be required, and this is what we found empirically to achieve maximum yields.
  • 28
    • 73649131219 scopus 로고    scopus 로고
    • Lewis acid catalyzed Newman-Kwart rearrangement: Fujii, K.; Shuto, Y.; Kinoshita, Y. Agric. Biol. Chem. 1990, 54, 2379-2384.
    • Lewis acid catalyzed Newman-Kwart rearrangement: Fujii, K.; Shuto, Y.; Kinoshita, Y. Agric. Biol. Chem. 1990, 54, 2379-2384.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.