Borane-Catalyzed Enantioselective α-Alkylation of Unactivated 2-Alkylbenzoxazoles with Electron-Deficient Olefins DOI

Chongren Ai,

Lu Liu, Xiaochen Wang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(35), С. 24663 - 24669

Опубликована: Авг. 20, 2024

Chiral borane–catalyzed reactions have recently emerged as a powerful tool for the enantioselective production of chiral scaffolds. In this study, we demonstrated first time that bisborane catalyst can be used α-functionalization 2-alkylazaarenes; specifically, accomplished unprecedented highly α-alkylation unactivated 2-alkylbenzoxazoles with electron-deficient olefins. The strong Lewis acidity and steric bulk were essential to observed reactivity selectivity.

Язык: Английский

A diversity of recently reported methodology for asymmetric imine reduction DOI Creative Commons
Jonathan Barrios-Rivera, Yingjian Xu, Martin Wills

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(20), С. 3312 - 3342

Опубликована: Янв. 1, 2020

This review describes recent developments in enantioselective imine reduction, including related substrates which a CN bond is the target for and in situ methods.

Язык: Английский

Процитировано

65

Chemo‐ and Enantioselective Hydrogenation of α‐Formyl Enamides: An Efficient Access to Chiral α‐Amido Aldehydes DOI
Jian Zhang, Jia Jia,

Xincheng Zeng

и другие.

Angewandte Chemie International Edition, Год журнала: 2019, Номер 58(33), С. 11505 - 11512

Опубликована: Июнь 13, 2019

Abstract In order to effectively synthesize chiral α‐amino aldehydes, which have a wide range of potential applications in organic synthesis and medicinal chemistry, highly chemo‐ enantioselective hydrogenation α‐formyl enamides has been developed, catalyzed by rhodium complex P‐stereogenic bisphosphine ligand. Under different hydrogen pressures, the α‐amido aldehydes β‐amido alcohols were obtained high yields (97–99 %) with excellent enantioselectivities (up >99.9 % ee ). The can be carried out on gram scale substrate/catalyst ratio 20 000 S/C), hydrogenated products further converted into several important products. Computations catalytic cycle gave clear description for R / S pathways, provided reasonable explanation enantioselectivity, revealed other specific features.

Язык: Английский

Процитировано

62

Asymmetric catalysis with FLPs DOI Creative Commons
Xiangqing Feng, Wei Meng, Haifeng Du

и другие.

Chemical Society Reviews, Год журнала: 2023, Номер 52(24), С. 8580 - 8598

Опубликована: Янв. 1, 2023

This review provides an overview of the important progress in FLP-catalyzed asymmetric reactions made over past 15 years, and both merits limitations FLP-catalysis have been highlighted.

Язык: Английский

Процитировано

21

Identifying Highly Active and Selective Cobalt X‐Ides for Electrocatalytic Hydrogenation of Quinoline DOI Open Access

Han Du,

Tianyi Wang, Meng Li

и другие.

Advanced Materials, Год журнала: 2024, Номер 36(41)

Опубликована: Сен. 2, 2024

Abstract Earth‐abundant Co X‐ides are emerging as promising catalysts for the electrocatalytic hydrogenation of quinoline (ECHQ), yet challenging due to limited fundamental understanding ECHQ mechanism on X‐ides. This work identifies catalytic performance differences in and provides significant insights into ECHQ. Among selected X‐ides, 3 O 4 presents best with a high conversion 98.2% 100% selectivity at ambient conditions. The sites present higher proportion 2‐coordinated hydrogen‐bonded water interface than other low negative potential, which enhances kinetics subsequent dissociation produce H*. An ideal 1,4/2,3‐H* addition pathway surface spontaneous desorption 1,2,3,4‐tetrahydroquinoline is demonstrated through operando tracing theoretical calculations. In comparison, 9 S 8 display lowest thermodynamic barrier H* formation step, suppresses hydrogenation; while Co(OH)F CoP undergo 1,2,3,4‐ 4,3/1,2‐H* respectively barriers thus quinoline. Moreover, wide substrate scope allows excellent derivatives N ‐heterocyclic substrates.

Язык: Английский

Процитировано

9

Ruthenium-Catalyzed Carbocycle-Selective Hydrogenation of Fused Heteroarenes DOI Creative Commons

Chenguang Luo,

Chao Wu, Xiaoming Wang

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 11, 2024

The homogeneous catalytic hydrogenation of benzo-fused heteroarenes generally provides partially hydrogenated products wherein the heteroaryl ring is preferentially reduced, such as quinoline hydrogenation, leading to 1,2,3,4-tetrahydroquinoline. Herein, we report a carbocycle-selective fused

Язык: Английский

Процитировано

8

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration DOI
Yong Wang,

Xinyi Cao,

Leyao Zhao

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(19), С. 4119 - 4129

Опубликована: Июль 22, 2020

Abstract A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H 2 combination, tolerated. activity reactants was studied trends follows: styrene>diphenylmethanimine>benzaldehyde>azobenzene>nitrobenzene>quinoline>acetophenone>benzonitrile . Substrates bearing two or more different were also investigated occurred with excellent chemoselectivity. Nano‐palladium catalyst in situ generated from Pd(OAc) extremely improved TH efficiency. Furthermore, chemoselective anti‐Markovnikov hydrodeuteration terminal olefins achieved D O via HD generation discrimination. magnified image

Язык: Английский

Процитировано

44

Ru clusters confined in Hydrogen-bonded organic frameworks for homogeneous catalytic hydrogenation of N-heterocyclic compounds with heterogeneous recyclability DOI
Qiang Song, Dan Xu, Wei David Wang

и другие.

Journal of Catalysis, Год журнала: 2021, Номер 406, С. 19 - 27

Опубликована: Сен. 29, 2021

Язык: Английский

Процитировано

39

Bifunctional Borane Catalysis of a Hydride Transfer/Enantioselective [2+2] Cycloaddition Cascade DOI
Ming Zhang, Xiaochen Wang

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(31), С. 17185 - 17190

Опубликована: Май 26, 2021

Abstract Herein, we present a mild and efficient method for synthesizing enantioenriched tetrahydroquinoline‐fused cyclobutenes through cascade reaction between 1,2‐dihydroquinolines alkynones with catalysis by chiral spiro‐bicyclic bisboranes. The bisboranes served two functions: first they catalyzed hydride transfer to convert the 1,2‐dihydroquinoline substrate 1,4‐dihydroquinoline, then activated alkynone an enantioselective [2+2] cycloaddition 1,4‐dihydroquinoline generated in situ.

Язык: Английский

Процитировано

38

Borane-Catalyzed Direct Asymmetric Vinylogous Mannich Reactions of Acyclic α,β-Unsaturated Ketones DOI

Jun‐Jie Tian,

Ning Liu,

Qi-Fei Liu

и другие.

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(8), С. 3054 - 3059

Опубликована: Фев. 11, 2021

Herein, we report that, by using chiral bicyclic bisborane catalysts, have achieved the first highly regio-, diastereo-, and enantioselective direct asymmetric vinylogous Mannich reactions of acyclic α,β-unsaturated ketones. The strong Lewis acidity steric bulk catalysts were essential for observed high yields selectivities.

Язык: Английский

Процитировано

36

Triarylborane-Catalyzed Reductive N-Alkylation of Amines: A Perspective DOI
Yoichi Hoshimoto, Sensuke Ogoshi

ACS Catalysis, Год журнала: 2019, Номер 9(6), С. 5439 - 5444

Опубликована: Май 3, 2019

Recent progress on the triarylborane (BAr3)-catalyzed reductive N-alkylation of amines is briefly summarized in this Perspective. The highlighted examples are divided into two main classes, that is, B(C6F5)3-catalyzed hydroamination alkynes and subsequent catalytic hydrogenation, as well BAr3-catalyzed carbonyl compounds such aldehydes, ketones, carboxylic acids presence hydrosilanes or molecular hydrogen. Key aspects several systems emphasized order to discuss reaction mechanisms, substrate scope, practical applications for preparation medicinal compounds, identification remaining challenges area.

Язык: Английский

Процитировано

43