Stille couplings catalytic in tin: Beyond proof-of-principle

Journal of the American Chemical Society

Volumn 122, Issue 2, 2000, Pages 384-385

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

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBON DIOXIDE; HALIDE; ORGANOTIN COMPOUND; PALLADIUM; TIN; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; MICROWAVE IRRADIATION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0343776202     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993446s     Document Type: Article

References (41)

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32. We assume the "Sn-O" species to be an organotin carbonate. However, this has yet to he firmly established.
33. 3SnH into hexabutylditin (Mitchell, T. N.; Amamria, A.; Killing, H.; Rutschow, D. J. Organomet. Chem. 1986, 304, 257-265) predominated the reaction. Furthermore, the addition of copper salts provided little or no improvement (see: (a) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749. (b) Han, X. J.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600- 7605).
34. 3SnH into hexabutylditin (Mitchell, T. N.; Amamria, A.; Killing, H.; Rutschow, D. J. Organomet. Chem. 1986, 304, 257-265) predominated the reaction. Furthermore, the addition of copper salts provided little or no improvement (see: (a) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749. (b) Han, X. J.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600- 7605).
35. 3SnH into hexabutylditin (Mitchell, T. N.; Amamria, A.; Killing, H.; Rutschow, D. J. Organomet. Chem. 1986, 304, 257-265) predominated the reaction. Furthermore, the addition of copper salts provided little or no improvement (see: (a) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749. (b) Han, X. J.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600-7605).
36. 3.
37. 2O gave the best yields.
38. We limited this study to α-trisubstituted alkynes containing a lone pair on one of the propargylic substituents as bulky alkynes give (E)-vinylstannanes upon Pd-catalyzed hydrostannylation. (See: (a) Blaskovich, M. A.; Kahn, M. J. Org. Chem. 1998, 63, 1119-1125. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768-7780.) Detailed studies of our protocol under less regiocontrolled circumstances are underway. We will report the results of these investigations as they develop.
39. We limited this study to α-trisubstituted alkynes containing a lone pair on one of the propargylic substituents as bulky alkynes give (E)- vinylstannanes upon Pd-catalyzed hydrostannylation. (See: (a) Blaskovich, M. A.; Kahn, M. J. Org. Chem. 1998, 63, 1119-1125. (b) Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 62, 7768-7780.) Detailed studies of our protocol under less regiocontrolled circumstances are underway. We will report the results of these investigations as they develop.
40. (a) Scott, W. J.; Moretto, A. F. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.; Wiley: New York, 1995; Vol 7, pp 5327-5328.
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