Reductive Removal of the Pivaloyl Protecting Group from Tetrazoles by a Naphthalene-Catalyzed Lithiation Process

Dedicated to the memory of Professor Alan R. Katritzky

Abstract

The reaction of various 1-pivaloyl-1H-tetrazoles with excess lithium and a catalytic amount of naphthalene (20 mol%) led, after treatment with methanol, to the corresponding free tetrazoles through reductive C–N bond cleavage. This methodology represents a reasonable alternative to other nonreductive protocols.

Keywords

tetrazoles - pivaloyl - lithium - deprotection

• References

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This methodology has been extensively used in our laboratories for the following applications: generation of organolithium compounds from non-halogenated materials,^12a preparation of very sensitive functionalized organolithium compounds,^12b–g reductive ring-opening of heterocycles,^12h–j generation of polylithium synthons,^{12k ,l} and for the activation of other metals,^12m especially nickel.^{12n, o} For reviews from our group, see:
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