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Literature DB >> 21812393

Ir(I)-catalyzed enantioselective secondary sp3 C-H bond activation of 2-(alkylamino)pyridines with alkenes.

Shiguang Pan¹, Kohei Endo, Takanori Shibata.

Abstract

A cationic Ir(I)-tolBINAP complex catalyzed an enantioselective C-C bond formation initiated by secondary sp(3) C-H bond cleavage adjacent to a nitrogen atom. The reaction of 2-(alkylamino)pyridines with various alkenes gave chiral amines in good yields with high enantiomeric excesses.

Entities: Chemical

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Year: 2011 PMID： 21812393 DOI： 10.1021/ol201907w

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

23 in total

1. Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

Authors: Kai-Jiong Xiao; Ling Chu; Gang Chen; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2016-06-10 Impact factor: 15.419

2. A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C-H Bonds.

Authors: Bo Su; Tai-Gang Zhou; Xian-Wei Li; Xiao-Ru Shao; Pei-Lin Xu; Wen-Lian Wu; John F Hartwig; Zhang-Jie Shi
Journal: Angew Chem Int Ed Engl Date: 2016-12-15 Impact factor: 15.336

3. Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Authors: Anh T Tran; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-07-24 Impact factor: 15.336

4. Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Authors: Taegyo Lee; Tyler W Wilson; Robert Berg; Per Ryberg; John F Hartwig
Journal: J Am Chem Soc Date: 2015-05-20 Impact factor: 15.419

Review 5. Enantioselective C(sp³)‒H bond activation by chiral transition metal catalysts.

Authors: Tyler G Saint-Denis; Ru-Yi Zhu; Gang Chen; Qing-Feng Wu; Jin-Quan Yu
Journal: Science Date: 2018-02-16 Impact factor: 47.728

Review 6. Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors: Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal: Top Curr Chem (Cham) Date: 2016-05-30

Ir(I)-catalyzed enantioselective secondary sp3 C-H bond activation of 2-(alkylamino)pyridines with alkenes.

1. Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

2. A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C-H Bonds.

3. Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

4. Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Review 5. Enantioselective C(sp³)‒H bond activation by chiral transition metal catalysts.

Review 6. Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

7. Iridium(I)-Catalyzed α-C(sp³)-H Alkylation of Saturated Azacycles.

8. α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Review 9. Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

10. Enantioselective C-H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution.

Review 5. Enantioselective C(sp3)‒H bond activation by chiral transition metal catalysts.

Review 6. Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Review 9. Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.

Review 5. Enantioselective C(sp³)‒H bond activation by chiral transition metal catalysts.