Dual Photoredox/Copper-Catalyzed Three-Component Alkylcyanation of Alkenes and 1,4-Alkylcyanation of 1,3-Enynes Employing Sulfoxonium Ylides as the Carbon Radical Precursors DOI
Zixuan Yang,

Xue‐Cen Xu,

Bowen He

et al.

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

Published: Dec. 3, 2024

A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl from sulfoxonium ylides adds to carbon-carbon double bonds styrenes or 1,3-enynes, generated benzylic allenyl radicals couple with a Cu(II) cyanide complex achieve selective cyanation. The reaction exhibits high chemo- regioselectivity wide substrate scope, providing an efficient method for synthesis nitriles in single step.

Language: Английский

Nickel-Catalyzed Reductive 1,4-Alkylacylation of 1,3-Enynes Enabling Synthesis of Allenyl Ketones DOI

Quanyuan Wang,

Keyi Peng,

Xupei Yao

et al.

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

Published: May 21, 2025

A nickel-catalyzed reductive 1,4-alkylacylation of 1,3-enynes has been established using nonactivated tertiary alkyl bromides and aromatic anhydrides as dual electrophiles. This protocol enables efficient assembly tetrasubstituted allenyl ketones with high chemo- regioselectivity. Mechanistic insights reveal the radical relay process involving synergistic interactions nickel zinc. The ketone products serve modular building blocks, particularly for constructing fully carbon-substituted furans via Au-catalyzed cycloisomerization selective 1,2-aryl migration, enhancing synthetic practicality.

Language: Английский

Citations

0
Visible light promoted synthesis of allenes DOI
Jitender Singh,

Barakha Saxena,

Anuj Sharma

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(18), P. 5143 - 5160

Published: Jan. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Language: Английский

Citations

3
Copper-Catalyzed Enantioselective Radical Cyanation of Allenic C(sp2)–H Bonds to Access Tri- and Tetrasubstituted Chiral Allenes DOI
Daqi Lv, Xiaotao Zhu, Hongli Bao

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7741 - 7748

Published: April 25, 2025

Language: Английский

Citations

0
Metallaphotoredox Synthesis of Axially Chiral Tetrasubstituted Allenes through Regio- and Enantioselective 1,4-Carbocyanation of 1,3-Enynes DOI

Keyi Peng,

Ya-Sheng Cao,

Quanyuan Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 14048 - 14057

Published: Sept. 10, 2024

Language: Английский

Citations

2
Dual Photoredox/Copper-Catalyzed Three-Component Alkylcyanation of Alkenes and 1,4-Alkylcyanation of 1,3-Enynes Employing Sulfoxonium Ylides as the Carbon Radical Precursors DOI
Zixuan Yang,

Xue‐Cen Xu,

Bowen He

et al.

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

Published: Dec. 3, 2024

A novel dual photoredox/copper-catalyzed three-component alkylcyanation of alkenes and 1,4-alkylcyanation 1,3-enynes have been developed. In this radical cyanoalkylation reaction, the photoredox induced alkyl from sulfoxonium ylides adds to carbon-carbon double bonds styrenes or 1,3-enynes, generated benzylic allenyl radicals couple with a Cu(II) cyanide complex achieve selective cyanation. The reaction exhibits high chemo- regioselectivity wide substrate scope, providing an efficient method for synthesis nitriles in single step.

Language: Английский

Citations

1