Thermally stable lithium alkynyl(triisopropoxy)borates were reacted with several aryl halides in the presence of palladium catalysts to give the corresponding cross-coupling products in excellent yields. The present methodology has been successfully applied to the antifungal terbinafine synthesis.
Pt(0)-Catalyzed Alkynylation of Aryl Iodides with Lithium Alkynyltriisopropoxy Borates.
β Scribed by Chang Ho Oh; V. Raghava Reddy
- Publisher
- John Wiley and Sons
- Year
- 2005
- Weight
- 21 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0931-7597
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Scheme 1. Synthesis of trifluorovinylarenes by cross-coupling. Scheme 2. Preparation of lithium trimethoxy(trifluorovinyl)borate 1 from HFC-134a.
A palladium(0)-tricyclohexylphosphine catalyzes cis-selective alkylative and arylative cyclization of alkyne-containing electron-deficient alkenes with organoboron reagents to provide five-or six-membered rings with exo tri-or tetra-substituted alkenes. The opposite stereoselectivity to that for the