2-Benzyloxymethyl-5-(tributylstannyl)tetrazole. A reagent for the preparation of 5-aryl- and 5-heteroaryl-1H-tetrazoles via the Stille reaction

2-Benzyloxymethyl-5-(tributylstannyl)tetrazole (2) is a useful reagent for the conversion of aryl- and heteroaryl-halides (bromides and iodides) to 5-aryl- and 5-heteroaryl-1H-tetrazoles. The conversion entails a copper(I) iodide co-catalyzed Stille palladium-catalyzed cross-coupling reaction and a N-benzyloxymethyl deprotection step. Coupling was possible with electron neutral and electron poor substrates in yields ranging from 35–93%.