Abstract
AbstractA phosphine‐free nickel(II)‐catalyzed method for the C(2)−H bond alkynylation of (benzo)thiazoles, (benz)imidazoles, and oxazoles is described. Well‐defined and air‐stable (Phen)NiCl2 catalyst efficiently catalyzes the coupling of diverse azoles with alkynyl bromides without the use of a copper co‐catalyst, and the method tolerates synthetically important functional groups. Preliminary mechanistic studies on this NiII‐catalyzed alkynylation emphasize the homogeneous nature of the catalyst, and rule out a radical manifold for the reaction. The synthetic utility of this Ni‐catalyzed method is demonstrated by further functionalizing the alkynylated benzothiazoles to 3‐methyl‐2‐(alkynyl)benzo[d]thiazolium salts that are known DNA cleaving agents.
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