| アイテムタイプ |
itemtype_ver1(1) |
| 公開日 |
2024-07-04 |
| タイトル |
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|
タイトル |
Facile Generation of tert-Butoxycarbonyl Chloride Equivalent and Its Use in Microflow Reactor |
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言語 |
en |
| 著者 |
Miyamoto, Kana
Okabe, Ren
Fuse, Shinichiro
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| アクセス権 |
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|
アクセス権 |
open access |
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アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 権利 |
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|
権利情報 |
This document is the Accepted Manuscript version of a Published Work that appeared in final form in [Organic Process Research & Development], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [https://pubs.acs.org/articlesonrequest/AOR-YDZY6ZITGUQZVIHXW2GY].” |
|
言語 |
en |
| 内容記述 |
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|
内容記述タイプ |
Abstract |
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内容記述 |
tert-Butyl carbamates, carbonates, and carbonothioates are useful as bioactive compounds, functional polymers, and synthetic intermediates for a variety of valuable organic compounds. The most conventional approach for the preparation of these tert-butoxycarbonyl (Boc)-containing compounds includes a nucleophilic acyl substitution reaction using commercially available and stable di-tert-butyl dicarbonate (Boc2O). However, this method usually requires a long reaction time and high-temperature conditions because of the mild electrophilicity of Boc2O. The use of highly electrophilic BocCl and its equivalent (BocX) allows the rapid and mild preparation of Boc-containing compounds. However, BocX is unstable, which has hampered its use. Herein, we report a rapid, mild, and facile preparation of BocX from triphosgene, t-BuOH, and two different types of bases, N-methylmorpholine and N-methylimidazole in a microflow reactor. The in situ-generated BocX was immediately used for the formation of carbamates, carbonates, and a carbonothioate. The role of the two different bases was also investigated. The developed approach showed a significantly better performance than that using Boc2O. |
|
言語 |
en |
| 出版者 |
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出版者 |
ACS Publications |
|
言語 |
en |
| 言語 |
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|
言語 |
eng |
| 資源タイプ |
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資源タイプresource |
http://purl.org/coar/resource_type/c_6501 |
|
タイプ |
journal article |
| 出版タイプ |
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出版タイプ |
AM |
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出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| 関連情報 |
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|
関連タイプ |
isVersionOf |
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|
識別子タイプ |
DOI |
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|
関連識別子 |
https://doi.org/10.1021/acs.oprd.4c00009 |
| 収録物識別子 |
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収録物識別子タイプ |
PISSN |
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収録物識別子 |
1083-6160 |
| 書誌情報 |
en : Organic Process Research & Development
巻 28,
号 5,
p. 1971-1978,
発行日 2024-05-17
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| ファイル公開日 |
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|
日付 |
2025-05-17 |
|
日付タイプ |
Available |
revised_manuscript_without_yellow_color_highlights.pdf (656 KB)
