Chiral Phosphine-Olefin Bidentate Ligands in Asymmetric Catalysis: Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl Boronic Acids to Maleimides

2005 ◽  
Vol 44 (29) ◽  
pp. 4611-4614 ◽  
Author(s):  
Ryo Shintani ◽  
Wei-Liang Duan ◽  
Takashi Nagano ◽  
Atsushi Okada ◽  
Tamio Hayashi
Keyword(s):  
Asymmetric Catalysis ◽  
Boronic Acids ◽  
Bidentate Ligands

Chiral Phosphine-Olefin Bidentate Ligands in Asymmetric Catalysis: Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl Boronic Acids to Maleimides

2005 ◽  
Vol 117 (29) ◽  
pp. 4687-4690 ◽  
Author(s):  
Ryo Shintani ◽  
Wei-Liang Duan ◽  
Takashi Nagano ◽  
Atsushi Okada ◽  
Tamio Hayashi
Keyword(s):  
Asymmetric Catalysis ◽  
Boronic Acids ◽  
Bidentate Ligands

Chiral Phosphine—Olefin Bidentate Ligands in Asymmetric Catalysis: Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl Boronic Acids to Maleimides.

ChemInform ◽  
2005 ◽  
Vol 36 (48) ◽  
Author(s):  
Ryo Shintani ◽  
Wei-Liang Duan ◽  
Takashi Nagano ◽  
Atsushi Okada ◽  
Tamio Hayashi
Keyword(s):  
Asymmetric Catalysis ◽  
Boronic Acids ◽  
Bidentate Ligands

scholarly journals Practical iridium-catalyzed direct α-arylation of N-heteroarenes with (hetero)arylboronic acids by H2O-mediated H2 evolution

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Liang Cao ◽  
He Zhao ◽  
Rongqing Guan ◽  
Huanfeng Jiang ◽  
Pierre. H. Dixneuf ◽  
...  
Keyword(s):  
Structural Modification ◽  
Universal Access ◽  
Boronic Acids ◽  
Direct Access ◽  
Bidentate Ligands ◽  
H2 Evolution ◽  
Arylboronic Acids ◽  
Coupling Strategy ◽  
General Method ◽  
Operational Simplicity

AbstractDespite the widespread applications of 2-(hetero)aryl N-heteroarenes in numerous fields of science and technology, universal access to such compounds is hampered due to the lack of a general method for their synthesis. Herein, by a H2O-mediated H2-evolution cross-coupling strategy, we report an iridium(III)-catalyzed facile method to direct α-arylation of N-heteroarenes with both aryl and heteroaryl boronic acids, proceeding with broad substrate scope and excellent functional compatibility, oxidant and reductant-free conditions, operational simplicity, easy scalability, and no need for prefunctionalization of N-heteroarenes. This method is applicable for structural modification of biomedical molecules, and offers a practical route for direct access to 2-(hetero)aryl N-heteroarenes, a class of potential cyclometalated C^N ligands and N^N bidentate ligands that are difficult to prepare with the existing α-C-H arylation methods, thus filling an important gap in the capabilities of synthetic organic chemistry.

scholarly journals Asymmetric Suzuki-Miyaura coupling of heterocycles via Rhodium-catalysed allylic arylation of racemates

2017 ◽  
Vol 8 (1) ◽  
Author(s):  
Philipp Schäfer ◽  
Thomas Palacin ◽  
Mireia Sidera ◽  
Stephen P. Fletcher
Keyword(s):  
Asymmetric Catalysis ◽  
Anticancer Agent ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Biologically Active ◽  
Advanced Materials ◽  
Industrial Sectors ◽  
Single Isomer ◽  
Carbon Carbon Bonds ◽  
Drug Synthesis

Abstract Using asymmetric catalysis to simultaneously form carbon–carbon bonds and generate single isomer products is strategically important. Suzuki-Miyaura cross-coupling is widely used in the academic and industrial sectors to synthesize drugs, agrochemicals and biologically active and advanced materials. However, widely applicable enantioselective Suzuki-Miyaura variations to provide 3D molecules remain elusive. Here we report a rhodium-catalysed asymmetric Suzuki-Miyaura reaction with important partners including aryls, vinyls, heteroaromatics and heterocycles. The method can be used to couple two heterocyclic species so the highly enantioenriched products have a wide array of cores. We show that pyridine boronic acids are unsuitable, but they can be halogen-modified at the 2-position to undergo reaction, and this halogen can then be removed or used to facilitate further reactions. The method is used to synthesize isoanabasine, preclamol, and niraparib—an anticancer agent in several clinical trials. We anticipate this method will be a useful tool in drug synthesis and discovery.

A new type of ferrocene-based phosphine-tert-butylsulfinamide ligand: synthesis and application in asymmetric catalysis

RSC Advances ◽  
2015 ◽  
Vol 5 (45) ◽  
pp. 35888-35892 ◽  
Author(s):  
Jiangwei Ma ◽  
Chuang Li ◽  
Dongxu Zhang ◽  
Yang Lei ◽  
Muqiong Li ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Bidentate Ligands ◽  
New Type ◽  
Ligand Synthesis

The first example of P,S-bidentate ligands containing both a planar chiral scaffold and a chiral sulfinamide moiety were reported.

Ferrocene phosphane-heteroatom/carbon bidentate ligands in asymmetric catalysis

2014 ◽  
Vol 43 (44) ◽  
pp. 16557-16579 ◽  
Author(s):  
Štefan Toma ◽  
Jana Csizmadiová ◽  
Mária Mečiarová ◽  
Radovan Šebesta
Keyword(s):  
Asymmetric Catalysis ◽  
Bidentate Ligands

A review of chiral ferrocene ligands featuring a combination of phosphorus and other elements as donor atoms in the asymmetric catalysis.

New methods in asymmetric catalysis based on new hemi-labile bidentate ligands

2008 ◽  
Vol 80 (5) ◽  
pp. 881-890 ◽  
Author(s):  
André B. Charette ◽  
Alexandre Côté ◽  
Jean-Nicolas Desrosiers ◽  
Isabelle Bonnaventure ◽  
Vincent N. G. Lindsay ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Nucleophilic Addition ◽  
Conjugate Addition ◽  
Bidentate Ligands ◽  
New Methods ◽  
Conjugate Reduction ◽  
Nitro Derivatives

Chiral bidentate hemi-labile bis(phosphine) monoxide ligands were shown to be quite effective in various copper-catalyzed transformations. Among them, the nucleophilic addition to imines, the conjugate addition to α,β-unsaturated nitro derivatives, and the conjugate reduction of α,β-unsaturated sulfones generally gave good to excellent yields and high enantiomeric excesses.

scholarly journals Practical Iridium-Catalyzed Direct α-arylation of N-heteroarenes with (Hetero)arylboronic Acids by H2O-Mediated H2 Evolution

2021 ◽  
Author(s):  
Liang Cao ◽  
He Zhao ◽  
Rongqing Rongqing ◽  
Huanfeng Jiang ◽  
Pierre Dixneuf ◽  
...  
Keyword(s):  
Structural Modification ◽  
Universal Access ◽  
Boronic Acids ◽  
Direct Access ◽  
Bidentate Ligands ◽  
H2 Evolution ◽  
Arylboronic Acids ◽  
Coupling Strategy ◽  
General Method ◽  
Operational Simplicity

Abstract Despite the widespread applications of 2-(hetero)aryl N-heteroarenes in numerous fields of science and technology, universal access to such compounds is easily hampered due to the lack of a general method for their synthesis. Herein, by a H2O-mediated H2-evolution cross-coupling strategy, we report a new iridium(III)-catalyzed facile method to direct α-arylation of N-heteroarenes with both aryl and heteroaryl boronic acids, proceeding with broad substrate scope and excellent functional compatibility, oxidant and reductant-free conditions, operational simplicity, easy scalability, and no need for prefunctionalization of N-heteroarenes. This method offers applicability for structural modification of biomedical molecules, but also a practical route for direct access to 2-(hetero)aryl N-heteroarenes, a class of potential cyclometalated C^N ligands and N^N bidentate ligands that are inaccessible or difficult to prepare with the existing α-C-H arylation methods, thus filling an important gap in the capabilities of synthetic organic chemistry.

scholarly journals Bis-Cyclometalated Indazole and Benzimidazole Chiral-at-Iridium Complexes: Synthesis and Asymmetric Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1822
Author(s):  
Sebastian Brunen ◽  
Yvonne Grell ◽  
Philipp S. Steinlandt ◽  
Klaus Harms ◽  
Eric Meggers
Keyword(s):  
Asymmetric Catalysis ◽  
Coordination Sphere ◽  
Conjugate Addition ◽  
Chiral Auxiliary ◽  
Iridium Complexes ◽  
Bidentate Ligands ◽  
Nazarov Cyclization ◽  
Tert Butyl ◽  
New Class ◽  
Acyl Imidazole

A new class of bis-cyclometalated iridium(III) catalysts containing two inert cyclometalated 6-tert-butyl-2-phenyl-2H-indazole bidentate ligands or two inert cyclometalated 5-tert-butyl-1-methyl-2-phenylbenzimidazoles is introduced. The coordination sphere is complemented by two labile acetonitriles, and a hexafluorophosphate ion serves as a counterion for the monocationic complexes. Single enantiomers of the chiral-at-iridium complexes (>99% er) are obtained through a chiral-auxiliary-mediated approach using a monofluorinated salicyloxazoline and are investigated as catalysts in the enantioselective conjugate addition of indole to an α,β-unsaturated 2-acyl imidazole and an asymmetric Nazarov cyclization.

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