Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks DOI
Weiwei Luo, Yu Zhang,

Meijun Ming

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6819 - 6849

Published: Jan. 1, 2024

This review highlights recent advances in the atroposelective preparation of axially chiral azole derivatives, emphasizing mechanistic insights and synthetic applications development this class five-membered heterocyclic frameworks.

Language: Английский

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

Chuang Hou,

Guòan Tai, Yi Liu

et al.

Deleted Journal, Journal Year: 2023, Volume and Issue: 2, P. e9120051 - e9120051

Published: Jan. 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.

Language: Английский

Citations

100

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

Tian‐Zhen Li,

Si‐Jia Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(3)

Published: Nov. 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.

Language: Английский

Citations

81

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

Yiming Yang,

Changhui Wu,

Junhao Xing

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(9), P. 6283 - 6293

Published: Feb. 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.

Language: Английский

Citations

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

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(14), P. 9713 - 9723

Published: July 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.

Language: Английский

Citations

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

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: July 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.

Language: Английский

Citations

36

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

Antoine Domain

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

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

Language: Английский

Citations

15

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

Weipeng Xu,

Shuaishuai Song

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(8)

Published: Jan. 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.

Language: Английский

Citations

11

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

Wen‐Tao Zhang,

Jixiang Yang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 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.

Language: Английский

Citations

9

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

Bo Yang,

Suqiong Yan,

Shirong Ban

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110837 - 110837

Published: Jan. 1, 2025

Language: Английский

Citations

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

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(24), P. 16300 - 16306

Published: Dec. 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.

Language: Английский

Citations

15