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

ABSTRACT: A base- and catalyst-free C(sp³)-H allylic alkylation of 2-alkylpyridines with Morita-Baylis-Hillman (MBH) carbonates is described. A plausible mechanism of the reaction might involve a tandem S_N2' 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.

SUBMITTER: Wang S

PROVIDER: S-EPMC8491709 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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

Wang Siyu S Zheng Lianyou L Wang Shutao S Ning Shulin S Zhang Zhuoqi Z Xiang Jinbao J

Beilstein journal of organic chemistry 20211001

A base- and catalyst-free C(sp3)-H allylic alkylation of 2-alkylpyridines with Morita-Baylis-Hillman (MBH) carbonates is 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 fo ...[more]

PMID: 34646399

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