C-C Bond Activation and Demethylenation of Epoxides by Amine Radical Dications

被引：4

作者：

Holt, Eric ^{[1
,2
]}

Garrison, Nathaniel G. ^{[1
,2
]}

Rowshanpour, Rozhin ^{[1
,2
]}

Kim, Justin Jeeyoung ^{[1
,2
]}

Henriquez, Nicolas ^{[1
,2
]}

Lam, Winson ^{[1
,2
]}

Kiame, Neil ^{[1
,2
]}

Williams, Jack ^{[1
,2
]}

Zhao, Sherrie ^{[1
,2
]}

Dudding, Travis ^{[1
,2
]}

Lectka, Thomas ^{[1
,2
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

[2] Brock Univ, Dept Chem, St Catharines, ON L2S3A1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 11期

基金：

美国国家科学基金会; 加拿大自然科学与工程研究理事会;

关键词：

CLEAVAGE;

D O I：

10.1021/acs.joc.3c00605

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this note, we explore a unique reactivity pattern that involves a rare radical-based C-C bond scission of epoxides followed by demethylenation. The reaction is accomplished by Selecfluor and its radical dication working in tandem; a mechanism supported by experiment and DFT calculations is proposed that involves the generation and identification of a key reactive intermediate. The reaction seems to be fairly general for 1,1-disubstituted epoxides.

引用

页码：7597 / 7600

页数：4

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