Short communicationUnexpected formation of 2-alkynylpyridines from iodo-selenopyridines by selective activation of CSe over CI bonds

Add time:09/10/2019    Source:sciencedirect.com

The synthesis of bicyclic 2-alkynylpyridines is performed in the presence of iodo-selenopyridines and terminal alkynes, using a palladium(II) catalyst, a copper(I) co-catalyst, and triethylamine as a base. This facile cross-coupling reaction leads to a wide variety of 2-alkynylpyridines in good yields. Mechanistic investigations provided by DFT calculations reveal that the reaction should involve a key selective activation of the CSe bond of the 2-selenopyridyl moiety by the in situ generated Pd(0) catalyst, preferentially to the CI bond activation. A transmetalation step with copper acetylide, followed by a reductive elimination, affords the 2-alkynylpyridine product.

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