Catalytic Atroposelective Synthesis of C−N Axially Chiral Aminophosphines via Dynamic Kinetic Resolution DOI
Carlos Rodríguez-Franco, Esther Roldán‐Molina, Alberto Aguirre‐Medina

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(37)

Опубликована: Июнь 25, 2024

A ruthenium-catalyzed reductive amination via asymmetric transfer hydrogenation (ATH) has been used to perform an efficient dynamic kinetic resolution (DKR) of N-aryl 2-formyl pyrroles decorated with a phosphine moiety positioned at the ortho' position. The strategy relies on labilization stereogenic axis in substrate facilitated by transient Lewis acid-base interaction (LABI) between carbonyl carbon and phosphorus center. reaction features broad scope aliphatic amines pyrrole scaffolds, proceeds under very mild conditions afford P,N atropisomers good high yields excellent enantioselectivities (up 99 % ee) for both diphenyl dicyclohexylphosphino derivatives.

Язык: Английский

Borophene-based materials for energy, sensors and information storage applications DOI Creative Commons

Chuang Hou,

Guòan Tai, Yi Liu

и другие.

Deleted Journal, Год журнала: 2023, Номер 2, С. e9120051 - e9120051

Опубликована: Янв. 5, 2023

Borophene, as a rising-star monoelemental two-dimensional (2D) material, has motivated great interest because of its novel properties, such anisotropic plasmonics, high carrier mobility, mechanical compliance, optical transparency, ultrahigh thermal conductance, and superconductivity. These properties make it an ideal candidate for use in the field energy, sensors, information storage. Stimulated by realization pioneering experimental works 2015 follow-up synthesis experiments, series high-performance borophene-based devices fields, including supercapacitors, batteries, hydroelectric generators, humidity gas pressure memories, have been experimentally reported recent years, which are beneficial to transition materials from practical application. Therefore, addition paying attention preparation borophene, significant efforts needed promote advancement related applications borophene. In this review, after providing brief overview borophene evolution synthesis, we mainly summarize energy storage, conversion, harvesting, Finally, based on current research status, some rational suggestions discussions issues challenges future direction proposed.

Язык: Английский

Процитировано

102

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field DOI
Hong‐Hao Zhang,

Tian‐Zhen Li,

Si‐Jia Liu

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(3)

Опубликована: Ноя. 2, 2023

With the rapid development of asymmetric catalysis, demand for enantioselective synthesis complex and diverse molecules with different chiral elements is increasing. Owing to unique features atropisomerism, catalytic atropisomers has attracted a considerable interest from chemical science community. In particular, introducing additional elements, such as carbon centered chirality, heteroatomic planar helical into provides an opportunity incorporate new properties axially compounds, thus expanding potential applications atropisomers. Thus, it important perform transformations synthesize bearing multiple elements. spite challenges in transformations, recent years, chemists have devised powerful strategies under organocatalysis or metal synthesizing wide range enantioenriched Therefore, become emerging field. This review summarizes progress this field indicates challenges, thereby promoting horizon.

Язык: Английский

Процитировано

83

Developing Biarylhemiboronic Esters for Biaryl Atropisomer Synthesis via Dynamic Kinetic Atroposelective Suzuki–Miyaura Cross-Coupling DOI

Yiming Yang,

Changhui Wu,

Junhao Xing

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(9), С. 6283 - 6293

Опубликована: Фев. 21, 2024

We herein introduce biarylhemiboronic esters as a new type of bridged biaryl reagent for asymmetric synthesis axially chiral structures, and the palladium-catalyzed Suzuki-Miyaura cross-coupling is developed. This dynamic kinetic atroposelective coupling reaction exhibits high enantioselectivity, good functional group tolerance, broad substrate scope. The synthetic application current method was demonstrated by transformations product programmed polyarene. Preliminary mechanistic studies suggested that proceeded via an enantio-determining transmetalation step.

Язык: Английский

Процитировано

18

Cobaltaelectro-Catalyzed C–H Annulation with Allenes for Atropochiral and P-Stereogenic Compounds: Late-Stage Diversification and Continuous Flow Scale-Up DOI Creative Commons
Lin Ye, Tristan von Münchow, Lutz Ackermann

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(14), С. 9713 - 9723

Опубликована: Июль 11, 2023

The 3d metallaelectro-catalyzed C-H activation has been identified as an increasingly viable strategy to access valuable organic molecules in a resource-economic fashion under exceedingly mild reaction conditions. However, the development of enantioselective is very challenging and its infancy. Here, we disclose merger cobaltaelectro-catalyzed with asymmetric catalysis for highly annulation allenes. A broad range C-N axially chiral P-stereogenic compounds were thereby obtained good yields up 98% high enantioselectivities >99% ee. practicality this approach was demonstrated by diversification complex bioactive drug well decagram scale electrocatalysis continuous flow.

Язык: Английский

Процитировано

41

Diversity-oriented synthesis of P-stereogenic and axially chiral monodentate biaryl phosphines enabled by C-P bond cleavage DOI Creative Commons

Liangzhi Pang,

Zhan Huang,

Qilin Sun

и другие.

Nature Communications, Год журнала: 2023, Номер 14(1)

Опубликована: Июль 24, 2023

Chiral monodentate biaryl phosphines (MOPs) have attracted intense attention as chiral ligands over the past decades. However, creation of structurally diverse MOPs with both P- and axial chirality is still in high demand but challenging. Here, we show a distinct strategy for diversity-oriented synthesis containing enabled by enantioselective C-P bond cleavage. The key PdII intermediates, generated through stereoselective oxidative addition bond, could be trapped alkynes, R3Si-Bpin, diboron esters or reduced H2O/B2pin2, leading to enantioenriched excellent diastereo- enantioselectivities. Based on outstanding properties parent scaffolds, axially serve catalysts asymmetric [3 + 2] annulation MBH carbonate affording functionalized bicyclic imide.

Язык: Английский

Процитировано

36

Enantioselective synthesis of molecules with multiple stereogenic elements DOI Creative Commons
Arthur Gaucherand, Expédite Yen‐Pon,

Antoine Domain

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(22), С. 11165 - 11206

Опубликована: Янв. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Язык: Английский

Процитировано

17

Enantioselective Rhodium‐Catalyzed C−H Arylation Enables Direct Synthesis of Atropisomeric Phosphines DOI
Zexian Li,

Weipeng Xu,

Shuaishuai Song

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(8)

Опубликована: Янв. 6, 2024

Atropisomeric phosphines hold considerable significance in asymmetric catalysis, yet their synthesis presents a formidable challenge owing to intricate multistep procedures. In this context, groundbreaking methodology has been presented for preparation. This innovative approach entails an atroposelective rhodium-catalyzed C-H activation employing aryl and heteroaryl halides, chelated by P(III) center. The essence of strategy lies its ability directly construct chiral phosphine ligands single step, thereby exhibiting exceptional efficiency terms atom redox economy. Illustrative examples serve demonstrate the immense potential situ-formed catalysis. Mechanistic experiments have further provided invaluable insights into transformation.

Язык: Английский

Процитировано

11

Synthesis of Alkene Atropisomers with Multiple Stereogenic Elements via Catalytic Asymmetric Rearrangement of 3‐Indolylmethanols DOI
Ping Wu,

Wen‐Tao Zhang,

Jixiang Yang

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Июль 23, 2024

Abstract Catalytic enantioselective preparation of alkene atropisomers with multiple stereogenic elements and discovery their applications have become significant but challenging issues in the scientific community due to unique structures this class atropisomers. We herein report first catalytic atroposelective cyclopentenyl[ b ]indoles, a new kind atropisomers, point axial chirality via an unusual rearrangement reaction 3‐indolylmethanols under asymmetric organocatalysis. Notably, novel type promising developing chiral ligands or organocatalysts, discovering antitumor drug candidates fluorescence imaging materials. Moreover, theoretical calculations elucidated possible mechanism non‐covalent interactions control enantioselectivity. This approach offers synthetic strategy for elements, represents 3‐indolylmethanols, which will advance chemistry indole chemistry.

Язык: Английский

Процитировано

10

New horizons in phosphorus-based emitters: From circularly polarized fluorescence to room-temperature phosphorescence DOI

Bo Yang,

Suqiong Yan,

Shirong Ban

и другие.

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 110837 - 110837

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

1

Thiourea-Assisted Chiral Bicyclic Imidazole Organocatalysts: Design, Synthesis, and Application in Asymmetric Acylative Desymmetrization of Bisphenols for the Construction of P-Stereocenters DOI
Chenglong Hu, Xuyang Tang,

Baochi Zhang

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(24), С. 16300 - 16306

Опубликована: Дек. 6, 2023

Thiourea-assisted chiral bicyclic imidazole organocatalysts were designed, synthesized, and successfully applied in the asymmetric acylative desymmetrization of P-prochiral bisphenols. Under mild conditions, P-stereogenic products obtained high yields (up to 99% yield) with enantioselectivities ee). Most importantly, reaction could also achieve satisfactory results under 1 mol % catalyst loadings. Mechanistic studies showed that synergistic effect including covalent activation acyl group by nucleophilic noncovalent H-bonding π-interaction between substrate was crucial for efficient construction P-stereocenters.

Язык: Английский

Процитировано

15