Direct C(sp3)-H allylation of 2-alkylpyridines with Morita-Baylis-Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement

Submitting author affiliation:
Jilin University, Changchun, China

Beilstein Arch. 2021, 202152.

Published 21 Jul 2021



A base- and catalyst-free C(sp3) – H allylic alkylation of 2-alkylpyridines with Morita-Baylis-Hillman (MBH) carbonates was described. A plausible mechanism of the reaction might involve a tandem SN2’ type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26-91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives.

Keywords: 2-alkylpyridines; Morita-Baylis-Hillman carbonates; allylic alkylation; aza-Cope rearrangement; catalyst-free.

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Wang, S.; Zheng, L.; Wang, S.; Ning, S.; Zhang, Z.; Xiang, J. Beilstein Arch. 2021, 202152. doi:10.3762/bxiv.2021.52.v1

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