Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature

Journal of the American Chemical Society

Volumn 118, Issue 11, 1996, Pages 2748-2749

  Allred, Gary D ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029979566     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9541239     Document Type: Article

References (29)

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19. A synthetically powerful process based on transmetalation from organostannanes to higher order cuprates is well-known: Behling, J.; Babiak, K.; Ng, J.; Campbell, A.; Moretti, R ; Koerner, M.; Lipshutz, B J. Am. Chem. Soc. 1988, 110, 2641. Behlina, J ; Ng, J.; Babiak, K.; Campbell, A., Elsworth, E., Lipshutz, B. Tetrahedron Lett. 1989, 30, 27.
20. A synthetically powerful process based on transmetalation from organostannanes to higher order cuprates is well-known: Behling, J.; Babiak, K.; Ng, J.; Campbell, A.; Moretti, R ; Koerner, M.; Lipshutz, B J. Am. Chem. Soc. 1988, 110, 2641. Behlina, J ; Ng, J.; Babiak, K.; Campbell, A., Elsworth, E., Lipshutz, B. Tetrahedron Lett. 1989, 30, 27.
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26. 3SnX
27. See Supporting Information for complete details.
28. From control experiments, it was determined that a large excess of CuCl (but not CuBr, CuI, or CuCN) will induce interinolecular crosscoupling of organostannanes and alkenyl iodides. In contrast to the use of 1.5 equiv of CuTC, more than 5 equiv of CuCl is required to drive the reaction to completion.
29. The addition of 2 5 equiv of CuTC to β-iodostyrene in NMP gave 1,4-diphenylbutadiene in 95% yield after only 30 mm at room temperature. A study of this mild Ullman-like coupling of alkeneyl iodides is underway (cf.; Cohen, T.; Cristea, I. J. Am Chem. Soc. 1976, 98, 748).