Highly regio- and stereoselective hydrostannylation of propargyl alcohols and ethers using dibutylchlorostannane and lithium chloride

Synlett

Volumn , Issue 3, 2005, Pages 406-410

  Miura, Katsukiyo ^a   Wang, Di ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Alcohols; Alkynes; Cross coupling; Hydrostannations; Radical reactions

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL ALCOHOL; CHLORINE DERIVATIVE; DIBUTYLCHLOROSTANNANE; ETHER DERIVATIVE; LITHIUM CHLORIDE; PALLADIUM; TIN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; CROSS COUPLING REACTION; HYDROSTANNYLATION; ISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 14644409712     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837219     Document Type: Article

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42. 3, TBAF (1.0 M in THF, 1.5 mmol), and a haloarene (0.550 mmol) were added successively to the reaction mixture obtained by the hydrostannylation of 1a or 8c (0.500 mmol). After being stirred at 60 °C for a given time, the resultant mixture was cooled to r.t. and diluted with t-BuOMe (10 mL). After addition of DBU (0.5 mL), the mixture was stirred for 5-10 min, passed through a short silica gel column, and evaporated. Purification of the residual oil was performed by silica gel column chromatography.
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