Difluorocarbene‐Induced Ring Opening of Tetrahydrofuran with TMSCF2Br for Difluoromethoxybutylation of N‐Aryl‐N‐hydroxylamines

In this work, a novel difluorocarbene‐induced ring opening of THF with TMSCF2Br for difluoromethoxybutylation of N‐aryl‐N‐hydroxylamines under mild conditions is reported. The mechanism study revealed that THF was intermolecular activated by difluorocarbene, then the formed oxonium ylide was nucleop...

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Published inEuropean journal of organic chemistry Vol. 2022; no. 30
Main Authors Zhu, Xinjie, Wei, Jun, Hu, Chenxian, Xiao, Qitao, Cai, Lvtao, Wang, Hao, Xie, Yuanyuan, Sheng, Rong
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 12.08.2022
Subjects
Aromatic compounds
Difluorocarbene
Difluoromethoxybutylation
Ring opening
Synthetic methods
Tetrahydrofuran
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Summary:In this work, a novel difluorocarbene‐induced ring opening of THF with TMSCF2Br for difluoromethoxybutylation of N‐aryl‐N‐hydroxylamines under mild conditions is reported. The mechanism study revealed that THF was intermolecular activated by difluorocarbene, then the formed oxonium ylide was nucleophilic attacked by N‐aryl‐N‐hydroxylamines. An operationally simple protocol for difluoromethoxybutylation of N‐aryl‐N‐hydroxylamines has been developed. TMSCF2Br was used as the difluorocarbene source and THF was used as both solvent and reactant. The reaction was carried out in air without transition‐metal catalysis.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200629