Abstract
1H-Tetrazoles occupy an important role in modern medicinal chemistry, but few methods for their modification exist. Many extant protocols require the use of a difficult to remove N-alkyl-protecting group, precluding the products from use as carboxylate bioisosteres, the major role of tetrazoles in pharmaceuticals. We herein report a convenient, protecting-group-free lithiation-substitution protocol for benzylic tetrazoles. Metalation with n-BuLi at 0 °C followed by electrophilic trapping gave a range of α-functionalized benzyltetrazoles in up to 91% yield.
| Original language | English |
|---|---|
| Pages (from-to) | 7069-7072 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 17 |
| Early online date | 26 Aug 2019 |
| DOIs | |
| Publication status | Published - 6 Sep 2019 |
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Profiles
Graeme Barker
- School of Engineering & Physical Sciences - Assistant Professor
- School of Engineering & Physical Sciences, Institute of Chemical Sciences - Assistant Professor
Person: Academic (Research & Teaching)
Cite this
Wong, J. Y. F., Lewandowska, A., Trowse, B., & Barker, G. (2019). Lithiation Substitution of Unprotected Benzyltetrazoles. Organic Letters, 21(17), 7069-7072. https://doi.org/10.1021/acs.orglett.9b02633