Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: a quaternary carbon atom makes the difference.
作者信息
Lavallo Vincent, Canac Yves, Präsang Carsten, Donnadieu Bruno, Bertrand Guy
机构信息
UCR-CNRS Joint Research Chemistry Laboratory (UMR 2282), Department of Chemistry, University of California, Riverside, CA 92521-0403, USA.
出版信息
Angew Chem Int Ed Engl. 2005 Sep 5;44(35):5705-9. doi: 10.1002/anie.200501841.
Abstract
摘要
相似文献
1
Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: a quaternary carbon atom makes the difference.
Angew Chem Int Ed Engl. 2005 Sep 5;44(35):5705-9. doi: 10.1002/anie.200501841.
2
CO fixation to stable acyclic and cyclic alkyl amino carbenes: stable amino ketenes with a small HOMO-LUMO gap.
Angew Chem Int Ed Engl. 2006 May 19;45(21):3488-91. doi: 10.1002/anie.200600987.
3
A rigid cyclic (alkyl)(amino)carbene ligand leads to isolation of low-coordinate transition-metal complexes.
Angew Chem Int Ed Engl. 2005 Nov 11;44(44):7236-9. doi: 10.1002/anie.200502566.
4
Synthesis of stable isothiazole carbenes.
Angew Chem Int Ed Engl. 2007;46(17):3118-21. doi: 10.1002/anie.200604305.
5
Arylation of rhodium(II) azavinyl carbenes with boronic acids.
J Am Chem Soc. 2012 Sep 12;134(36):14670-3. doi: 10.1021/ja3062453. Epub 2012 Aug 28.
6
Synthesis of a simplified version of stable bulky and rigid cyclic (alkyl)(amino)carbenes, and catalytic activity of the ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives.
J Am Chem Soc. 2009 Jun 24;131(24):8690-6. doi: 10.1021/ja902051m.
7
Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.
J Am Chem Soc. 2006 Feb 8;128(5):1472-3. doi: 10.1021/ja058222q.
8
Template synthesis of a coordinated tetracarbene ligand with crown ether topology.
Angew Chem Int Ed Engl. 2005 Jun 13;44(24):3759-63. doi: 10.1002/anie.200462690.
9
The chemistry of functionalised N-heterocyclic carbenes.
Chem Soc Rev. 2007 Apr;36(4):592-607. doi: 10.1039/b603765h. Epub 2006 Sep 8.
10
Synthesis of transient and stable C-amino phosphorus ylides and their fragmentation into transient and stable carbenes.
J Am Chem Soc. 2006 Jan 18;128(2):459-64. doi: 10.1021/ja055863c.
引用本文的文献
1
IPaul - spatially-defined, wingtip-flexible, N,C-chelating oxazole and thiazole donor N-heterocyclic carbene ligands.
Dalton Trans. 2025 Aug 13. doi: 10.1039/d5dt01576f.
2
Gold(I) Complexes of ImPyDippDipp and ImPyMesMes: Biaryl L‑Shaped N‑Heterocyclic Carbene Analogues of IPr and IMes.
Organometallics. 2025 May 15;44(10):1100-1107. doi: 10.1021/acs.organomet.5c00093. eCollection 2025 May 26.
3
Aluminacyclopropene-phosphine complex: a carbene-exchange reagent.
Chem Sci. 2025 Jun 30. doi: 10.1039/d5sc03846d.
4
Unique selectivity of rare-earth metal ambiphilic carbenes towards organic molecules and novel reactivity patterns with isonitriles.
Chem Sci. 2025 May 23. doi: 10.1039/d5sc01502b.
5
Diboron-Incorporated Indenofluorene: Isolation of Crystalline Neutral and Reduced States of 6,12-Diboraindeno[1,2-]fluorene.
J Am Chem Soc. 2025 Jun 4;147(22):18431-18437. doi: 10.1021/jacs.5c04487. Epub 2025 May 21.
6
Phosphinoisocyanide/Alkyne Cycloaddition: Generation of Azaphospholylidene (NPHC) Ligands.
Angew Chem Int Ed Engl. 2025 Jul 7;64(28):e202504620. doi: 10.1002/anie.202504620. Epub 2025 May 24.
7
Multi-site reduction of hexachlorophosphazene to low-valent PN heterocycles and extension to the reduction of poly-chlorophosphazene.
Chem Sci. 2025 Apr 24. doi: 10.1039/d4sc07559e.
8
β-Lactam Ylidenes: An Overlooked Class of N-Heterocyclic Carbenes.
Chemistry. 2025 Jun 3;31(31):e202501320. doi: 10.1002/chem.202501320. Epub 2025 May 8.
9
IPr*: Sterically Adaptable Dinuclear N-Heterocyclic Carbenes.
Inorg Chem. 2025 Apr 28;64(16):7851-7857. doi: 10.1021/acs.inorgchem.5c01013. Epub 2025 Apr 15.
10
A Joyful Journey: Tungsten(VI) and Tungsten(V) Fluorides Meet N-Heterocyclic Carbenes and Cyclic (Alkyl)(Amino)Carbenes.
Angew Chem Int Ed Engl. 2025 Jun 17;64(25):e202504498. doi: 10.1002/anie.202504498. Epub 2025 May 15.
本文引用的文献
1
A defined N-heterocyclic carbene complex for the palladium-catalyzed Suzuki cross-coupling of aryl chlorides at ambient temperatures.
Angew Chem Int Ed Engl. 2002 Apr 15;41(8):1363-5. doi: 10.1002/1521-3773(20020415)41:8<1363::aid-anie1363>3.0.co;2-g.
2
Diaminocarbene- and Fischer-carbene complexes of palladium and nickel by oxidative insertion: preparation, structure, and catalytic activity.
Chemistry. 2005 Mar 4;11(6):1833-53. doi: 10.1002/chem.200400928.
3
Aryl palladium carbene complexes and carbene-aryl coupling reactions.
Chemistry. 2005 Feb 18;11(5):1565-73. doi: 10.1002/chem.200400811.
4
The development of efficient catalysts for palladium-catalyzed coupling reactions of aryl halides.
Chem Commun (Camb). 2005 Jan 28(4):431-40. doi: 10.1039/b410937f. Epub 2004 Dec 20.
5
Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis.
Chem Soc Rev. 2004 Nov 30;33(9):619-36. doi: 10.1039/b406802p. Epub 2004 Nov 3.
6
Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis.
J Am Chem Soc. 2004 Nov 24;126(46):15195-201. doi: 10.1021/ja045349r.
7
When and how do diaminocarbenes dimerize?
Angew Chem Int Ed Engl. 2004 Nov 12;43(44):5896-911. doi: 10.1002/anie.200400654.
8
Nucleophilic carbenes in asymmetric organocatalysis.
Acc Chem Res. 2004 Aug;37(8):534-41. doi: 10.1021/ar030050j.
9
Synthesis, reactivity, and ligand properties of a stable alkyl carbene.
J Am Chem Soc. 2004 Jul 21;126(28):8670-1. doi: 10.1021/ja047503f.
10
An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature.
Angew Chem Int Ed Engl. 2003 Aug 11;42(31):3690-3. doi: 10.1002/anie.200351325.
Zotero 插件