Development of the Suzuki−Miyaura Cross-Coupling Reaction: Use of Air-Stable Potassium Alkynyltrifluoroborates in Aryl Alkynylations
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- 30 October 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (24) , 8416-8423
- https://doi.org/10.1021/jo0262356
Abstract
The palladium-catalyzed cross-coupling reaction of potassium alkynyltrifluoroborates with aryl halides or triflates proceeds readily with moderate to excellent yields. The potassium alkynyltrifluoroborates are air- and moisture-stable crystalline solids that can be stored indefinitely, which will provide an advantage in applications to combinatorial chemistry. The alkynyl cross-coupling reaction can be effected using 9 mol % of PdCl2(dppf)·CH2Cl2 as catalyst in THF or THF−H2O in the presence of Cs2CO3 as the inorganic base. A variety of functional groups are tolerated in both partners.Keywords
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