Abstract
| 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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Lithiation Substitution of Unprotected Benzyltetrazoles. / Wong, Jeff Y. F.; Lewandowska, Agnieszka; Trowse, Benjamin; Barker, Graeme.
In: Organic Letters, Vol. 21, No. 17, 06.09.2019, p. 7069-7072.Research output: Contribution to journal › Article
TY - JOUR
T1 - Lithiation Substitution of Unprotected Benzyltetrazoles
AU - Wong, Jeff Y. F.
AU - Lewandowska, Agnieszka
AU - Trowse, Benjamin
AU - Barker, Graeme
PY - 2019/9/6
Y1 - 2019/9/6
N2 - 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.
AB - 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.
U2 - 10.1021/acs.orglett.9b02633
DO - 10.1021/acs.orglett.9b02633
M3 - Article
VL - 21
SP - 7069
EP - 7072
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 17
ER -