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

  1. Siyu Wang,
  2. Lianyou ZhengORCID Logo,
  3. Shutao Wang,
  4. Shulin Ning,
  5. Zhuoqi Zhang and
  6. Jinbao Xiang

Submitting author affiliation: Jilin University, Changchun, China

Beilstein Arch. 2021, 202152. https://doi.org/10.3762/bxiv.2021.52.v1

Published 21 Jul 2021

  • Preprint

Abstract

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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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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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