Air-Stable Oxyallyl Patterns and a Switchable N-Heterocyclic Carbene

被引：9

作者：

Tomas-Mendivil, Eder ^{[1
]}

Devillard, Marc ^{[1
,2
]}

Regnier, Vianney ^{[1
]}

Pecaut, Jacques ^{[3
]}

Martin, David ^{[1
]}

机构：

[1] Univ Grenoble Alpes, CNRS, DCM, F-38000 Grenoble, France

[2] Univ Rennes, CNRS, UMR6226, ISCR, F-35042 Rennes, France

[3] Univ Grenoble Alpes, CEA, INAC SyMMES, CNRS,UMR 5819, F-38000 Grenoble, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 28期

关键词：

metal complexes; oxyallyl species; stable carbenes; substituent effects; OLEFIN METATHESIS CATALYSTS; INDEPENDENT CHEMICAL-SHIFTS; PI-ACCEPTOR PROPERTIES; VINYL ALLENE OXIDE; DONOR PROPERTIES; CYCLOADDITION REACTIONS; CYCLOPENTYL OXYALLYL; AROMATICITY; LIGANDS; NHC;

D O I：

10.1002/anie.202002669

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxyallyl derivatives are typically elusive compounds. Even recently reported "stabilized" 1,3-diaminooxyallyl species are still highly reactive and have short lifetimes at room temperature. Herein, we report the synthesis and preliminary study of mesoionic pyrimidine derivatives that feature 1,3-bis(dimethylamino)oxyallyl patterns with an unprecedented level of stabilization. The latter are not only insensitive towards air and moisture, but they are also compatible with the formation of an ancillary stable N-heterocyclic carbene moiety. As the oxyallyl pattern is proton-responsive, it allows the reversible switching of the electronic properties of the carbene, as a ligand.

引用

页码：11516 / 11520

页数：5

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