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Literature DB >> 18776944

Toward phenanthridin-2-ylidene: electrophilicity versus acidity in planar-constrained C-aryl iminium salts.

Xavier Cattoën¹, Didier Bourissou, Guy Bertrand.

Abstract

-A phenanthridinium salt was prepared in four steps, including an intramolecular CH-arylation and a hydride abstraction reaction. Treatment with sterically demanding bases does not lead to the corresponding carbene, but rather to addition products: the planar-constrained geometry significantly enhances the electrophilicity over the acidity of C-aryl iminium salts.

Entities: Chemical Disease

Year: 2006 PMID： 18776944 PMCID： PMC2529453 DOI： 10.1016/j.tetlet.2005.11.052

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

18 in total

1. Stable Carbenes.

Authors: Didier Bourissou; Olivier Guerret; François P. Gabbaï; Guy Bertrand
Journal: Chem Rev Date: 2000-01-12 Impact factor: 60.622

2. (Amino)(aryl)carbenes: stable singlet carbenes featuring a spectator substituent.

Authors: S Solé; H Gornitzka; W W Schoeller; D Bourissou; G Bertrand
Journal: Science Date: 2001-06-08 Impact factor: 47.728

3. Stable versions of transient push-pull carbenes: extending lifetimes from nanoseconds to weeks

Authors:
Journal: Science Date: 2000-05-05 Impact factor: 47.728

4. Diaminocarbene- and Fischer-carbene complexes of palladium and nickel by oxidative insertion: preparation, structure, and catalytic activity.

Authors: Doris Kremzow; Günter Seidel; Christian W Lehmann; Alois Fürstner
Journal: Chemistry Date: 2005-03-04 Impact factor: 5.236

1. Intramolecular Ring-Expansion Reaction (RER) and Intermolecular Coordination of In Situ Generated Cyclic (Amino)(aryl)carbenes (cAArCs).

Authors: Jan Lorkowski; Mirjam Krahfuß; Maciej Kubicki; Udo Radius; Cezary Pietraszuk
Journal: Chemistry Date: 2019-08-02 Impact factor: 5.236

1 in total

Toward phenanthridin-2-ylidene: electrophilicity versus acidity in planar-constrained C-aryl iminium salts.

1. Stable Carbenes.

2. (Amino)(aryl)carbenes: stable singlet carbenes featuring a spectator substituent.

3. Stable versions of transient push-pull carbenes: extending lifetimes from nanoseconds to weeks

4. Diaminocarbene- and Fischer-carbene complexes of palladium and nickel by oxidative insertion: preparation, structure, and catalytic activity.

5. Abnormal binding in a carbene complex formed from an imidazolium salt and a metal hydride complex.

6. Stable non-push-pull phosphanylcarbenes: NMR spectroscopic characterization of a methylcarbene.

7. A general and versatile approach to thermally generated N-heterocyclic carbenes.

8. Nucleophilic carbenes in asymmetric organocatalysis.

9. Transient azomethine-ylides from a stable amino-carbene and an aldiminium salt.

10. N-heterocyclic carbenes: a new concept in organometallic catalysis.

1. Intramolecular Ring-Expansion Reaction (RER) and Intermolecular Coordination of In Situ Generated Cyclic (Amino)(aryl)carbenes (cAArCs).