Metal-free tetrahydrofuranylation of alcohols with tertbutyl nitrite

[Display omitted] •The protection of alcohols.•Synthesizing asymmetric ethers via tBuONO-promoted oxidative coupling between tetrahydrofuran and alcohols.•Exploring the potential applications of tertbutyl nitrite in the organic synthesis. Metal-free tetrahydrofuranylation of alcohols in the presence...

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Bibliographic Details
Published inTetrahedron letters Vol. 61; no. 34; pp. 152251 - 152253
Main Authors Bi, Kang, Cai, Yue-Ming, Zhou, Yun-Bing, Lin, Junyue, Liu, Miao-Chang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.08.2020
Elsevier
Subjects
Alkoxyl radical
Chemistry
Chemistry, Organic
Metal-free tetrahydrofuran
Physical Sciences
Protection of alcohols
Science & Technology
Tertbutyl nitrite
Alkoxyl radical
Protection of alcohols
Tertbutyl nitrite
Metal-free tetrahydrofuran
MILD
EFFICIENT CATALYST
TETRAHYDROPYRANYLATION
DEPROTECTION
DIRECT FACILE TETRAHYDROFURANYLATION
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Summary:[Display omitted] •The protection of alcohols.•Synthesizing asymmetric ethers via tBuONO-promoted oxidative coupling between tetrahydrofuran and alcohols.•Exploring the potential applications of tertbutyl nitrite in the organic synthesis. Metal-free tetrahydrofuranylation of alcohols in the presence of tertbutyl nitrite is described, providing a facile and green route for the protection of hydroxy groups. Mechanistic studies demonstrate that this transformation proceeds in a radical way, and involves alkyl nitrite of corresponding alcohol as the key intermediate.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152251