Stille couplings catalytic in tin: A "Sn-F" approach

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4173-4176

  Maleczka Jr , Robert E ^a   Gallagher, William P ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; TIN FLUORIDE; TRIMETHYLTIN;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; PALLADIUM; TIN FLUORIDES; TRIMETHYLTIN COMPOUNDS;

EID: 0035961041     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016792z     Document Type: Article

References (47)

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15. Tin toxicity has also spurred development of reactions with Zn (Negishi) and B (Suzuki) compounds (ref 1a, Chapters 1-2) as well as advances in Si (Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439-6440 and references cited. Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053-2055. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688) and In-based cross-couplings (Perez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155-4160).
16. Tin toxicity has also spurred development of reactions with Zn (Negishi) and B (Suzuki) compounds (ref 1a, Chapters 1-2) as well as advances in Si (Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439-6440 and references cited. Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053-2055. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688) and In-based cross-couplings (Perez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155-4160).
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43. 2 in one portion resulted in a 20% yield of 4.
44. Although tin-free preparations of 8 can be envisaged, prior work by us and the immediate availablity of intermediates favored the chosen route.
45. Under traditional Stille conditions the analogous vinyl iodide gave an intrusive amount of homocoupling.
46. Pd(0)-catalyzed hydrostannation of 4 exclusively gave the (E) isomer (88% yield).
47. 13C NMR spectral data, as well as appropriate ion identification by high-resolution mass spectrometry. See Supporting Information for details.