Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes** DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(32)

Published: June 15, 2023

Abstract We disclose a Ni‐catalyzed regioselective dialkylation reaction of alkenylarenes with α‐halocarbonyls and alkylzinc reagents. The produces γ‐arylated alkanecarbonyl compounds the generation two new C(sp 3 )−C(sp ) bonds at vicinal carbons alkenes. This is effective for use primary, secondary tertiary α‐halocarboxylic esters, amides ketones in conjunction primary reagents as sources terminal cyclic internal

Language: Английский

Visible-Light-Induced Photoredox 1,2-Dialkylation of Styrenes with α-Carbonyl Alkyl Bromides and Pyridin-1-ium Salts DOI

Chong‐Hui Xu,

Gui‐Fen Lv,

Jing‐Hao Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 281 - 290

Published: Dec. 18, 2023

A visible-light-driven photoredox dialkylation of styrenes with α-carbonyl alkyl bromides and pyridin-1-ium salts for the synthesis polysubstituted 1,4-dihydropyridines is reported. This reaction enables formation two new C(sp3)–C(sp3) bonds in a single step provides strategy that employs as functionalized alkylating reagents via dearomatization to directly trap resulting radicals from radical addition alkenes then terminate alkene dialkylation.

Language: Английский

Citations

5

Photocatalyst‐free Synthesis of Oxindoles and Isoquinolinediones via the Radical Reaction of N‐Arylacrylamides with Monoalkyl Cesium Oxalate Salts by Visible Light Catalysis DOI Open Access

Chenyue Zhao,

Jinli Xu, Dongping Cheng

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(45)

Published: Aug. 28, 2024

Abstract A photocatalyst‐free cascade reaction of N ‐alkyl‐ ‐arylmethacrylamides with monoalkyl cesium oxalate salts is described. In the presence visible light and (NH 4 ) 2 S O 8 , undergo single‐electron oxidation/CO extrusion to generate alkyl radicals, followed by addition subsequent cyclization give alkylated oxindoles. addition, ‐methacryloylbenzamides could be applied for reaction, providing a series isoquinolinediones, which are completely different from products obtained oxalates as substrates.

Language: Английский

Citations

1

Direct Alkene Functionalization via Photocatalytic Hydrogen Atom Transfer from C(sp3)–H Compounds: A Route to Pharmaceutically Important Molecules DOI

Hangqian Fan,

Yuxin Fang, Jingbo Yu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Direct functionalization of alkenes with C(sp

Language: Английский

Citations

1

Synthesis of Isoquinolinediones via the Radical Addition/Cyclization of N‐Alkyl‐N‐methacryloylbenzamides with Monoalkyl Oxalates DOI
Jinli Xu,

Chenyue Zhao,

Dongping Cheng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4527 - 4532

Published: Nov. 11, 2023

Abstract A photocatalytic reaction of N‐alkyl‐N‐methacryloylbenzamides with monoalkyl oxalates is described. Monoalkyl undergo single‐electron oxidation/CO 2 extrusion to generate alkoxycarbonyl radicals, followed by the addition and subsequent cyclization give substituted isoquinolinediones. wide variety were amenable in this protocol, affording various

Language: Английский

Citations

3

Ni-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes. Generation of Two Vicinal C(sp3)-C(sp3) Bonds Across Alkenes DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Published: March 24, 2023

We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with -halocarbonyls and alkylzinc reagents. The produces -arylated alkanecarbonyl compounds the generation two new C(sp3)-C(sp3) bonds at vicinal carbons alkenes. This is effective for use primary, secondary tertiary -halocarboxylic esters, amides ketones in conjunction primary reagents as sources C(sp3) terminal cyclic internal

Language: Английский

Citations

0

Asymmetric Synthesis of Unnatural α-Amino Acids through Photoredox-Mediated C–O Bond Activation of Aliphatic Alcohols DOI Creative Commons
Gregory R. Alvey, Elena V. Stepanova, Andrey Shatskiy

et al.

Published: May 15, 2023

An efficient protocol for the asymmetric synthesis of unnatural amino acids is realized through photoredox-mediated C–O bond activation oxalate esters derived from aliphatic alcohols as radical precursors. The developed system uses chiral glyoxylate-derived N-sulfinyl imine acceptor and allows quick access to a range functionalized an atom-economical redox-neutral process with CO2 only stoichiometric by-product.

Language: Английский

Citations

0

Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes** DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(32)

Published: June 15, 2023

Abstract We disclose a Ni‐catalyzed regioselective dialkylation reaction of alkenylarenes with α‐halocarbonyls and alkylzinc reagents. The produces γ‐arylated alkanecarbonyl compounds the generation two new C(sp 3 )−C(sp ) bonds at vicinal carbons alkenes. This is effective for use primary, secondary tertiary α‐halocarboxylic esters, amides ketones in conjunction primary reagents as sources terminal cyclic internal

Language: Английский

Citations

0