Coordination-Assisted Ni-Catalyzed Regio- and Enantioselective 1,2-Borylalkylation of Unactivated Alkenes DOI

Yuqin Zhu,

Zhetai Feng,

Wenyi Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein we successfully utilize various directing groups to achieve a ligand-enabled nickel-catalyzed 1,2-borylalkylation of unactivated alkenes. A β-amino alcohol was employed as the ligand for non-asymmetric alkenes, while bulky chiral diamine used asymmetric allyl amides.

Language: Английский

Enantioselective Copper-Catalyzed Three-Component Cascade Boronation–Dearomatization Reaction: Synthesis of Chiral Boron-Containing 1,4-Dihydropyridines DOI

Fazhou Yang,

Yujie Dong, Jinbao Wang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

A three-component cascade boronation–dearomatization reaction of alkenes, a diboron compound, and pyridinium salt is diclosed, affording chiral boron-containing 1,4-dihyropyridines in high yields (≤98%) diastereoselectivity (≤10:1 dr), along with excellent enantioselectivity (typically >99% ee). The catalytic system performs efficiently at low catalyst loadings (1 mol %) was tested >50 examples, including some biologically active molecules.

Language: Английский

Citations

0

Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents DOI Creative Commons
Qianqian Chang,

Qini Li,

Yi-Hui Deng

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 3, 2025

Language: Английский

Citations

0

Metallaphotoredox-Catalyzed Three-Component Asymmetric Cross-Electrophile Coupling for Chiral Boronate Synthesis DOI
Xiaofang Li, Yuntong Hu,

Zhonghou Huang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(20), P. 15790 - 15798

Published: Oct. 10, 2024

Here, we report a photoredox and nickel-catalyzed cross-electrophile coupling strategy for the asymmetric three-component 1,2-alkylarylation of vinyl boronates with (hetero)aryl bromides (2°, 3°)-alkyl redox-active esters in presence Hantzsch ester. With fluorinated pyridyl-substituted chiral biimidazoline ligand, this reaction enables straightforward access to wide variety synthetically valuable α-aryl from readily available starting materials. This features mild conditions, broad substrate generality, good functional group tolerance proceeds without using metal reductants or alkyl halides. Furthermore, alkenyl halides other electron-deficient alkenes such as acrylates phosphonates can be applied successfully. Preliminary mechanistic studies shed light on potential pathways roles organic amines.

Language: Английский

Citations

3

Enantioselective Borylative Functionalization of Internal Alkenes: A Platform for Constructing Vicinal Stereocenters DOI
Yu‐Jie Zhu, Jiaxin Li, Haotian Zhao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(24), P. 3588 - 3604

Published: Nov. 1, 2024

Comprehensive Summary Vicinal stereogenic centers are ubiquitous structural scaffolds in both natural products and synthetic compounds, yet their enantioselective construction remains a significant challenge organic synthesis. Organoboron compounds of paramount importance chemistry due to ability undergo facile transformations, yielding diverse essential chemical bonds such as carbon‐carbon, carbon‐oxygen, carbon‐nitrogen, carbon‐halogen bonds. Transition‐metal‐catalyzed asymmetric borylative functionalizations internal alkenes offer promising strategy for the installation two adjacent chiral across carbon‐carbon By leveraging versatile transformations newly introduced boryl unit, this approach holds great potential expanding diversity vicinal scaffolds. In concise review, we aim highlight recent advancements transition‐metal‐catalyzed alkenes, underscore utility constructing centers, discuss unsolved challenges future directions field. Key Scientists

Language: Английский

Citations

3

Coordination-Assisted Ni-Catalyzed Regio- and Enantioselective 1,2-Borylalkylation of Unactivated Alkenes DOI

Yuqin Zhu,

Zhetai Feng,

Wenyi Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein we successfully utilize various directing groups to achieve a ligand-enabled nickel-catalyzed 1,2-borylalkylation of unactivated alkenes. A β-amino alcohol was employed as the ligand for non-asymmetric alkenes, while bulky chiral diamine used asymmetric allyl amides.

Language: Английский

Citations

0