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Palladium-catalyzed coupling of aryl triflates with organostannanes

โœ Scribed by Echavarren, Antonio M.; Stille, J. K.

Book ID
120050641
Publisher
American Chemical Society
Year
1987
Tongue
English
Weight
984 KB
Volume
109
Category
Article
ISSN
0002-7863

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โœฆ Synopsis

The palladium-catalyzed coupling reaction of aryl triflates with alkyl, vinyl, acetylenic, and aryl tin reagents in the presence of lithium chloride takes place in high yields under mild conditions. However, allyltrialkyltin reagents coupled in lower yields, and unselective transfer of the allyl group was observed. The aryl coupling reaction was applied to a synthesis of the quinoline alkaloid dubamine. The palladium-catalyzed coupling of aryl triflates with hexamethylditin gave aryltrimethylstannanes or homocoupled products depending on the amount of tin reagent. p-Bromophenyl triflate could be coupled selectively with vinyltributyltin through either the carbon-halogen or the carbon-oxygen bond by using different palladium catalysts.

Herein we now report on the scope of the palladium-catalyzed cross-coupling reaction of aryl triflates with organostannanes.8-'0

(1) (a) Stille, J. K.

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