Palladium-Catalyzed Enantioselective Isodesmic C—H Iodination DOI Open Access
Senmiao Xu

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(9), P. 3325 - 3325

Published: Jan. 1, 2023

Language: Английский

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp3)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development DOI
Weijie Chen, Huiying Xu,

Fu‐Xiaomin Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(20)

Published: March 19, 2024

Abstract Herein, multiple types of chiral Os(II) complexes have been designed to address the appealing yet challenging asymmetric C(sp 3 )−H functionalization, among which Os(II)/Salox species is found be most efficient for precise stereocontrol in realizing amidation. As exemplified by enantioenriched pyrrolidinone synthesis, such tailored catalyst efficiently enables an intramolecular site‐/enantioselective amidation γ‐position dioxazolone substrates, benzyl, propargyl and allyl groups bearing various substituted forms are well compatible, affording corresponding γ‐lactam products with good er values (up 99 : 1) diverse functionality (>35 examples). The unique performance advantage developed system terms catalytic energy profile induction has further clarified integrated experimental computational studies.

Language: Английский

Citations

3
Carboxyl group assisted isodesmicmeta-C–H iodination of phenethylamines, benzylamines, and 2-aryl anilines DOI
Lei Yang, Xinchao Wang, Meng Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3760 - 3765

Published: Jan. 1, 2023

Remote isodesmic meta -C–H iodination of phenethylamines, benzylamines, and 2-aryl anilines was enabled by an alkyl carboxyl group.

Language: Английский

Citations

4
Selective C–H Iodination of Weinreb Amides and Benzamides through Iridium Catalysis in Solution and under Mechanochemical Conditions DOI Creative Commons
Amparo Sanz‐Marco, Beatriz Saavedra,

Elis Erbing

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(14), P. 2800 - 2805

Published: Nov. 6, 2023

The acid mediated ortho-iodination of Weinreb amides using a readily available catalyst is described. selective amides, challenging substrates in directed C–H activations, and also benzamides achieved. process works under mild conditions tolerates air moisture, having great potential for industrial applications. methodology can be applied mechanochemical maintaining the reaction outcome selectivity.

Language: Английский

Citations

4
Hyperconjugation‐Driven Isodesmic Reaction of Indoles and Anilines: Reaction Discovery, Mechanism Study, and Antitumor Application DOI Open Access
Yuqing Xiao,

Kai‐Xin Fang,

Zhihan Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(47)

Published: Aug. 23, 2024

Abstract Isodesmic reactions, in which chemical bonds are redistributed between substrates and products, provide a general powerful strategy for both biological synthesis. However, most isodesmic reactions involve either metathesis or functional‐group transfer. Here, we serendipitously discovered novel reaction of indoles anilines that proceeds intramolecularly under weakly acidic conditions. In this process, the five‐membered ring indole motif is broken new constructed on aniline side, accompanied by formation motif. Mechanistic studies revealed pivotal role σ→π* hyperconjugation nitrogen atom driving unusual reaction. Furthermore, successfully synthesized diverse series polycyclic derivatives; among quinolines, potential antitumor agents were identified using cellular vivo experiments, thereby demonstrating synthetic utility developed methodology.

Language: Английский

Citations

1
Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp3)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development DOI
Weijie Chen, Huiying Xu,

Fu‐Xiaomin Liu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(20)

Published: March 19, 2024

Abstract Herein, multiple types of chiral Os(II) complexes have been designed to address the appealing yet challenging asymmetric C(sp 3 )−H functionalization, among which Os(II)/Salox species is found be most efficient for precise stereocontrol in realizing amidation. As exemplified by enantioenriched pyrrolidinone synthesis, such tailored catalyst efficiently enables an intramolecular site‐/enantioselective amidation γ‐position dioxazolone substrates, benzyl, propargyl and allyl groups bearing various substituted forms are well compatible, affording corresponding γ‐lactam products with good er values (up 99 : 1) diverse functionality (>35 examples). The unique performance advantage developed system terms catalytic energy profile induction has further clarified integrated experimental computational studies.

Language: Английский

Citations

0
Palladium-catalyzed epoxidation of olefins using electrophiles as oxidizing agents DOI

Biao Yao,

Lujun Zhang, Yupeng Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4689 - 4696

Published: Jan. 1, 2024

The development of palladium-catalysed olefin epoxidation reactions using electrophilic reagents as oxidants: modular synthesis oxazolines. efficient esters, alcohols and halogen-containing products was achieved.

Language: Английский

Citations

0
Hyperconjugation‐Driven Isodesmic Reaction of Indoles and Anilines: Reaction Discovery, Mechanism Study, and Antitumor Application DOI Open Access
Yuqing Xiao,

Kai‐Xin Fang,

Zhihan Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(47)

Published: Aug. 23, 2024

Abstract Isodesmic reactions, in which chemical bonds are redistributed between substrates and products, provide a general powerful strategy for both biological synthesis. However, most isodesmic reactions involve either metathesis or functional‐group transfer. Here, we serendipitously discovered novel reaction of indoles anilines that proceeds intramolecularly under weakly acidic conditions. In this process, the five‐membered ring indole motif is broken new constructed on aniline side, accompanied by formation motif. Mechanistic studies revealed pivotal role σ→π* hyperconjugation nitrogen atom driving unusual reaction. Furthermore, successfully synthesized diverse series polycyclic derivatives; among quinolines, potential antitumor agents were identified using cellular vivo experiments, thereby demonstrating synthetic utility developed methodology.

Language: Английский

Citations

0
Palladium-Catalyzed Enantioselective Isodesmic C—H Iodination DOI Open Access
Senmiao Xu

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(9), P. 3325 - 3325

Published: Jan. 1, 2023

Language: Английский

Citations

0