Synthesis of α‐N‐Heteroaryl Ketones by Nickel‐Catalyzed Chemo‐, Regio‐ and Enantioselective Carbonylation of Alkenes and N‐Alkenyl Heteroarenes DOI Open Access
Xiaoyi Chen, Qiong Yu, Wei Shu

et al.

Angewandte Chemie, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Abstract Enantioenriched α‐aminoketones serve as important substructures in life science and precursors for the synthesis of diverse value‐added targets organic biochemistry. However, direct access to enantioenriched from simple readily available starting materials remains a formidable challenge. Herein, we report an unprecedented nickel‐catalyzed asymmetric cross‐coupling protocol α‐ N ‐heteroaryl ketones alkenes enamines presence carbon monoxide surrogate. The success this reaction relies on sorting two different along with control regio‐ enantioselectivity. This reductive‐oxidative carbonylation unactivated featuring use surrogate allows gas‐free streamlined assembly distinct alkenes.

Language: Английский

Iridium-Catalyzed Migratory Terminal C(sp3)–H Amidation of Heteroatom-Substituted Internal Alkenes via Olefin Chain Walking DOI
Qing Wang, Hoimin Jung, Dongwook Kim

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 31, 2023

Hydroamination facilitated by metal hydride catalysis is an appealing synthetic approach to access valuable nitrogen-containing compounds from readily available unsaturated hydrocarbons. While high regioselectivity can be achieved usually for substrates bearing polar chelation groups, the reaction involving simple alkenes frequently provides nonselective outcomes. Herein, we report iridium-catalyzed highly regioselective terminal C(sp3)-H amidation of internal utilizing dioxazolones as amino source via olefin chain walking. Most notably, this mechanistic motif double bond migration position operates not only with dialkyl-substituted including styrenes but also heteroatom-substituted olefins such enol ethers, vinyl silanes, and borons, thus representing first example methyl latter type through a nondissociative walking process.

Language: Английский

Citations

12
Synthesis of Enantioenriched 1,2‐cis Disubstituted Cycloalkanes by Convergent NiH Catalysis DOI
Changpeng Chen,

Wenqing Guo,

Deyong Qiao

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(36)

Published: July 20, 2023

Enantioenriched multi-substituted cycloalkanes constitute an essential class of compounds in pharmaceuticals, natural products and agrochemicals. Here we report NiH-catalyzed asymmetric migratory hydroalkylation process for the efficient selective construction such compounds. Through a dynamic kinetic transformation (DYKAT), easily accessible racemic isomeric mixtures cycloalkenes could be directly utilized as starting materials, convergently producing thermo-dynamically disfavored chiral 1,2-cis disubstituted bearing vicinal stereocenters with high levels regio-, diastereo- enantioselectivity. In addition, prochiral cyclic alkenes can also employed, deliver through desymmetrization process.

Language: Английский

Citations

11
Recent Progress in NiH-Catalyzed Linear or Branch Hydrofunctionalization of Terminal or Internal Alkenes DOI
Huimin Yang, Yang Ye

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(5)

Published: July 20, 2023

Language: Английский

Citations

11
Synthesis of α‐N‐Heteroaryl Ketones by Nickel‐Catalyzed Chemo‐, Regio‐ and Enantioselective Carbonylation of Alkenes and N‐Alkenyl Heteroarenes DOI Open Access
Xiaoyi Chen, Qiong Yu, Wei Shu

et al.

Angewandte Chemie International Edition, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Enantioenriched α-aminoketones serve as important substructures in life science and precursors for the synthesis of diverse value-added targets organic biochemistry. However, direct access to enantioenriched from simple readily available starting materials remains a formidable challenge. Herein, we report an unprecedented nickel-catalyzed asymmetric cross-coupling protocol α-N-heteroaryl ketones alkenes enamines presence carbon monoxide surrogate. The success this reaction relies on sorting two different along with control regio- enantioselectivity. This reductive-oxidative carbonylation unactivated featuring use surrogate allows gas-free streamlined assembly distinct alkenes.

Language: Английский

Citations

0
Synthesis of α‐N‐Heteroaryl Ketones by Nickel‐Catalyzed Chemo‐, Regio‐ and Enantioselective Carbonylation of Alkenes and N‐Alkenyl Heteroarenes DOI Open Access
Xiaoyi Chen, Qiong Yu, Wei Shu

et al.

Angewandte Chemie, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Abstract Enantioenriched α‐aminoketones serve as important substructures in life science and precursors for the synthesis of diverse value‐added targets organic biochemistry. However, direct access to enantioenriched from simple readily available starting materials remains a formidable challenge. Herein, we report an unprecedented nickel‐catalyzed asymmetric cross‐coupling protocol α‐ N ‐heteroaryl ketones alkenes enamines presence carbon monoxide surrogate. The success this reaction relies on sorting two different along with control regio‐ enantioselectivity. This reductive‐oxidative carbonylation unactivated featuring use surrogate allows gas‐free streamlined assembly distinct alkenes.

Language: Английский

Citations

0