Microwave-assisted one-pot hydrostannylation/Stille couplings

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3655-3658

  Maleczka Jr , Robert E ^a   Lavis, Jérôme M ^a   Clark, Damon H ^a   Gallagher, William P ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYNE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOTIN COMPOUND; PALLADIUM; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

ALKADIENES; ALKYNES; CATALYSIS; INDICATORS AND REAGENTS; MICROWAVES; ORGANOTIN COMPOUNDS; PALLADIUM; STYRENES;

EID: 0034676573     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006559l     Document Type: Article

References (38)

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17. See cautionary notes (vide infra).
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25. 4 was realized with this catalyst.
26. Subjecting internal alkynes to the reaction conditions resulted in the formation of complex mixtures.
27. Cinnamyl chloride and p-chloroaniline were also examined as potential coupling partners. However, under our standard conditions no Stille reactions were observed with these electrophiles. The performance of catalysts specifically designed to couple chlorides (see: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2413) will be discussed in a full account of this work.
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34. Reactions without AIBN proceeded but were less stereoselective.
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36. 4 varied in activity; occasionally necessitating a doubling of the catalyst load.
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38. Reactions run with 5 mmol alkyne in 5 mL of THF were prone to explode.