Rally from C to N: The goal of the race concerns connecting carbon and nitrogen. While the SN2‐type mechanism constitutes a one‐way road to produce CH3NH3+ from Zn(CH3)+ and NH3, activation of the CH bond of methane in the Zn(NH2)+/CH4 system is a blind alley (see scheme).

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In this communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron‐deficient alkynes, leading to synthetically useful β‐seleno derivativesand vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under “on water” conditions. When the addition occurs on a triple bond, good stereoselectivity is observed, and the reaction shows a rate acceleration in water suspension.

Vinyl selenides can be easily obtained through nucleophilic substitution of the corresponding halides by using PhSeZnCl in THF as well as “on water” conditions. The reaction is stereospecific with retention of the alkene geometry. The only exception has been observed in the reaction conducted on a β‐chloro‐α,β‐unsaturated ketone, which afforded the (Z) product starting from either the (E) or (Z) isomer. DFT calculations have been performed in order to investigate the reaction mechanism, the stereochemistry of the process and the role of the zinc atom. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)