Direct Oxidation of Csp3-H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow

被引：17

作者：

Lesieur, Mathieu ^{[1
]}

Battilocchio, Claudio ^{[2
,3
]}

Labes, Ricardo ^{[2
]}

Jacq, Jerome ^{[1
]}

Genicot, Christophe ^{[1
]}

Ley, Steven V. ^{[2
]}

Pasau, Patrick ^{[1
]}

机构：

[1] UCB Biopharma, Ave Ind, B-1420 Braine Lalleud, Belgium

[2] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

[3] Syngenta Crop Protect AG, Schaffhauserstr, CH-4332 Stein, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 05期

关键词：

dioxirane; flow; hydroxylation; oxidation; Oxone; TFDO; C-H BONDS; ALIPHATIC-AMINES; STRAIN RELEASE; HYDROXYLATION; OXYFUNCTIONALIZATION; REMOTE; METHYL(TRIFLUOROMETHYL)DIOXIRANE; FUNCTIONALIZATION; REACTIVITY; CATALYST;

D O I：

10.1002/chem.201805657

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A fast, scalable, and safer C-sp(3)-H oxidation of activated and un-activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp(3)-H bonds. The process exhibits a broad scope and good functional group compatibility (28 examples, 8-99 %). The scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane.

引用

页码：1203 / 1207

页数：5

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