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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| Published in | Tetrahedron letters Vol. 61; no. 34; pp. 152251 - 152253 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
20.08.2020
Elsevier |
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| Abstract | [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. |
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| AbstractList | 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. (C) 2020 Elsevier Ltd. All rights reserved. [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. |
| ArticleNumber | 152251 |
| Author | Lin, Junyue Liu, Miao-Chang Bi, Kang Cai, Yue-Ming Zhou, Yun-Bing |
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| Keywords | Alkoxyl radical Protection of alcohols Tertbutyl nitrite Metal-free tetrahydrofuran MILD EFFICIENT CATALYST TETRAHYDROPYRANYLATION DEPROTECTION DIRECT FACILE TETRAHYDROFURANYLATION |
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•The protection of alcohols.•Synthesizing asymmetric ethers via tBuONO-promoted oxidative coupling between tetrahydrofuran and... Metal-free tetrahydrofuranylation of alcohols in the presence of tertbutyl nitrite is described, providing a facile and green route for the protection of... |
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| SubjectTerms | Alkoxyl radical Chemistry Chemistry, Organic Metal-free tetrahydrofuran Physical Sciences Protection of alcohols Science & Technology Tertbutyl nitrite |
| Title | Metal-free tetrahydrofuranylation of alcohols with tertbutyl nitrite |
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