Development of a one-pot palladium-catalyzed hydrostannylation/Stille coupling protocol with catalytic amounts of tin

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9622-9623

  Maleczka Jr , Robert E ^a   Terstiege, Ina ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; PALLADIUM; TIN DERIVATIVE; TRIBUTYLTIN; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 20644449037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981915n     Document Type: Article

References (29)

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20. 2O occurs only at elevated temperatures (ref 8). Therefore, under our reaction conditions a 2-fold excess of bistributyltin oxide is required for complete consumption of the alkyne.
21. We observed no evidence of palladium-mediated hydrosilylation with PMHS, although other silanes, such as phenylsilane, did show a propensity for hydrosilylation.
22. 4 has proven an effective means for the in situ conversion of tin halides to tin hydrides in free radical reactions (
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24. (b) Curran, D. P. Synthesis 1988, 489-513 and references therein).
25. For our purposes though, this method appeared less than ideal as hydride reducing agents are known to reduce Pd(II) intermediates (Tsuji, J. Palladium Reagents and Catalysts; Wiley: Toronto, 1995; p 148). Furthermore, strong hydride donors would severely curtail the broad functional group tolerance normally associated with the Stille reaction.
26. More basic metal alkoxides (NaOMe, NaOPh, etc.) reacted with PMHS. Not surprisingly, application of such alkoxides to the hydrostannylation/Stille coupling with catalytic amounts of tin was largely unsuccessful.
27. The same reaction sequence absent tin produced no Stille coupling products, ruling out the Pd-mediated coupling of a transient vinylsilane with the halide ((a) Hosomi, A.; Kohra, S.; Tominaga, Y. Chem. Pharm. Bull. 1988, 36, 4622-4625.
28. (b) Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918-920).
29. 2Pd and diethyl ether proved to be the Pd catalyst and solvent of choice.