ChemInform Abstract: Nickel-Catalyzed Carbostannylation of Alkynes with Allyl-, Acyl-, and Alkynylstannanes: Stereoselective Synthesis of Trisubstituted Vinylstannanes.
Abstract
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ChemInform Abstract
The addition of alkynyl- (XVI), (XVIII), allyl- (I), (V), and acylstannanes (XIII) to both electron-deficient and electron-rich alkynes (II), (VI) is achieved in the presence of nickel catalysts. The reaction proceeds with high regio- and syn-selectivity to afford differently substituted alkenylstannanes in moderate to good yields. The synthetic utility of the obtained alkenylstannanes is demonstrated. Thus, they are suitable educts in the Heck reaction with aryl iodides, as shown for the formation of compound (X). Additionally, organylstannane (VIIb) can undergo, after iodination, palladium-catalyzed cyclo-carbonylation to afford methylenecyclopentenone derivative (XII).
