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Synthesis 2015; 47(04): 507-510
DOI: 10.1055/s-0034-1378681
DOI: 10.1055/s-0034-1378681
paper
Reductive Removal of the Pivaloyl Protecting Group from Tetrazoles by a Naphthalene-Catalyzed Lithiation Process
Weitere Informationen
Publikationsverlauf
Received: 09. Oktober 2014
Accepted: 22. Oktober 2014
Publikationsdatum:
27. November 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201504/lookinside/thumbnails/10.1055-s-0034-1378681-1.jpg)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379457.
- Supporting Information
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References
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See, for instance:
For reviews, see:
For mechanistic studies, see:
For a polymer version of this reaction, see:
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: