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Sulfonylation of 1,4-Diazabicyclo[2.2.2]octane: Charge-Transfer Complex Triggered C-N Bond Cleavage.

ABSTRACT: A novel charge-transfer complex triggered sulfonylation of 1,4-diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge-transfer complex between electron-withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of N-ethylated piperazine sulfonamide in good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the charge-transfer complex formation between sulfonyl chlorides and DABCO, which facilitates the C-N bond cleavage of DABCO.

SUBMITTER: Fu Y

PROVIDER: S-EPMC6350051 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Sulfonylation of 1,4-Diazabicyclo[2.2.2]octane: Charge-Transfer Complex Triggered C-N Bond Cleavage.

Fu Ying Y Xu Qin-Shan QS Li Quan-Zhou QZ Li Ming-Peng MP Shi Chun-Zhao CZ Du Zhengyin Z

ChemistryOpen 20190128 1

A novel charge-transfer complex triggered sulfonylation of 1,4-diazabicyclo[2.2.2]octane (DABCO) with mild reaction conditions has been developed. The formation of a charge-transfer complex between electron-withdrawing (hetero)aryl sulfonyl chloride and DABCO allows the synthesis of <i>N</i>-ethylated piperazine sulfonamide in good yields. The reaction has a high functional group tolerance. Spectroscopic studies confirmed the charge-transfer complex formation between sulfonyl chlorides and DABCO ...[more]

PMID: 30723657

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Multiple Roles of 1,4-Diazabicyclo[2.2.2]octane in the Solvothermal Synthesis of Iodobismuthates.

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