We report a general preparation ofheteroarylmethylzinc chloridesby direct zinc insertion into heteroarylmethyl chlorides, along witha facile and straightforward synthesis of these heterocyclic chloromethylprecursors. We demonstrate that heteroarylmethylzinc reagents undergovarious reactions including cross-couplings, allylations, acylations,and addition reactions to aldehydes, leading to polyfunctional heterocyclicproducts. Furthermore, these heteroaromatic zinc compounds prove tobe versatile reagents for the preparation of various N- and O-heterocyclesand give access to an analogue of a CB1 modifier. [ABSTRACT FROM AUTHOR]