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三光气-胺碱促进的脂肪族伯醇的氯化反应。

Triphosgene-amine base promoted chlorination of unactivated aliphatic alcohols.

机构信息

Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, USA.

出版信息

J Org Chem. 2013 Apr 19;78(8):3989-96. doi: 10.1021/jo400341n. Epub 2013 Mar 29.

DOI:10.1021/jo400341n
PMID:23496045
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4153350/
Abstract

Unactivated α-branched primary and secondary aliphatic alcohols have been successfully transformed into their corresponding alkyl chlorides in high yields upon treatment with a mixture of triphosgene and pyridine in dichloromethane at reflux. These mild chlorination conditions are high yielding, stereospecific, and well tolerated by numerous sensitive functionalities. Furthermore, no nuisance waste products are generated in the course of the reactions.

摘要

未活化的α-支链伯、仲脂肪醇在回流的二氯甲烷中与三光气和吡啶的混合物作用下,高产率地转化成相应的烷基氯。这些温和的氯化条件产率高、立体专一性好,并且能耐受许多敏感官能团。此外,反应过程中不会生成讨厌的废物。

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本文引用的文献

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Org Lett. 2012 Jul 20;14(14):3676-9. doi: 10.1021/ol301520d. Epub 2012 Jul 10.
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Design, synthesis, and structure-activity relationship studies of conformationally restricted mutilin 14-carbamates.设计、合成及构效关系研究受限型多利菌素 14-氨基甲酸酯。
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氯原子控制的末端环氧化物引发的双环化级联反应可用于合成强效细胞毒素 Haterumaimides J 和 K。
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Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.三光气-吡啶介导的无环脂肪族1,3-二醇的立体选择性氯化反应
Chem Commun (Camb). 2015 Oct 18;51(81):15075-8. doi: 10.1039/c5cc06365e.
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