Enantioselective catalytic radical decarbonylative azidation and cyanation of aldehydes DOI Creative Commons
Rui Wang, Chengyu Wang, Peng Liu

et al.

Science Advances, Journal Year: 2023, Volume and Issue: 9(35)

Published: Sept. 1, 2023

Empowered by the ubiquity of carbonyl functional groups in organic compounds, decarbonylative functionalization was prevalent construction complex molecules. Under this context, asymmetric has emerged as an efficient pathway to accessing chiral motifs. However, ablation enantiomeric control a conventional 2e transition metal–catalyzed process notable because harsh conditions (high temperatures, etc.) that are usually required. To address challenge and use readily accessible aldehyde directly, we report radical azidation cyanation. Diverse aldehydes were directly used alkyl precursor, engaging subsequent inner-sphere or outer-sphere ligand transfer where motifs (CN N 3 ) could be incorporated excellent site- enantioselectivity. Mild conditions, broad scope, regioselectivity (driven polarity-matching strategy), enantioselectivity shown for both transformations. This strategy using precursor offered powerful reaction manifold transformations construct regio- stereoselectively.

Language: Английский

Recent Advances in Enantioselective Radical Reactions of C(sp3)—H Bond DOI
Ling Tang,

Haitao Qin,

Feng Liu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 498 - 498

Published: Jan. 1, 2025

Language: Английский

Citations

0
Electrochemical Mn-catalyzed nitrogenation of alkynes to nitriles via C C bonds cleavage DOI

Yuwei Liang,

Jianwei Huang, Zhiqiang Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111166 - 111166

Published: April 1, 2025

Language: Английский

Citations

0
A Metal-Free Oxidative Azidation Method for Selective Azidation of C(sp3)–H Bonds and Diazidation of Alkenes DOI

Yihang Bai,

Yong Li,

Xuehan Yu

et al.

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

Published: May 21, 2025

Current metal-free methods for the synthesis of alkyl (1,2-di)azides mainly rely on highly reactive hypervalent iodine reagents and electrochemical methods, which require specialized devices. Herein, we show a robust Selectfluor-promoted oxidative azidation method, can effectively achieve selective C(sp3)-H bonds in alkanes/methylarenes diazidation alkenes, without involving any metal catalyst additive. The utility this method is highlighted by broad substrate scope, late-stage functionalization, gram-scale synthesis. Mechanistic studies indicate that reaction proceeds via radical process.

Language: Английский

Citations

0
Tempo-Catalyzed Electrochemical Hydrobenzylation of Imines with Methylarenes Via Radical Cascade Reaction DOI

Kaifa Zhang,

Kun Xia, Hui Chen

et al.

Published: Jan. 1, 2025

Language: Английский

Citations

0
Enantioselective catalytic radical decarbonylative azidation and cyanation of aldehydes DOI Creative Commons
Rui Wang, Chengyu Wang, Peng Liu

et al.

Science Advances, Journal Year: 2023, Volume and Issue: 9(35)

Published: Sept. 1, 2023

Empowered by the ubiquity of carbonyl functional groups in organic compounds, decarbonylative functionalization was prevalent construction complex molecules. Under this context, asymmetric has emerged as an efficient pathway to accessing chiral motifs. However, ablation enantiomeric control a conventional 2e transition metal–catalyzed process notable because harsh conditions (high temperatures, etc.) that are usually required. To address challenge and use readily accessible aldehyde directly, we report radical azidation cyanation. Diverse aldehydes were directly used alkyl precursor, engaging subsequent inner-sphere or outer-sphere ligand transfer where motifs (CN N 3 ) could be incorporated excellent site- enantioselectivity. Mild conditions, broad scope, regioselectivity (driven polarity-matching strategy), enantioselectivity shown for both transformations. This strategy using precursor offered powerful reaction manifold transformations construct regio- stereoselectively.

Language: Английский

Citations

6