DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy DOI

Si‐Wei Tian,

Zhentao Luo,

Biquan Xiong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6774 - 6778

Published: Jan. 1, 2024

A novel and attractive photochemical difunctionalization of N -tosyl acrylamide for constructing alkylsulfonylated oxindoles amides with excellent substrate adaptability via a radical Smiles rearrangement strategy is described.

Language: Английский

Citations

7
Radical Cascade Annulation of Biphenyl Acrylamides to Dibenzoazepinones: Experimental and DFT Studies DOI

Raju Dupud,

Ramakrishnan Thushara,

Karthik Kumar Merugu

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(31)

Published: June 6, 2024

Abstract An efficient method for the conversion of biphenyl acrylamides to dibenzoazepinones with −SCF 3 incorporation is described. This operationally simple radical cascade reaction employs CAN as an oxidant and exhibits good functional group tolerance. Substrates featuring −OCH , −CH −Br or −Cl at para ‐position aromatic ring a preference ipso ‐cyclization due intervention DMSO in reaction. Density theory (DFT) calculations provide valuable insights into reaction's energetics product selectivity.

Language: Английский

Citations

1
Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr2 Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization DOI
Jinhui Cai,

Kaili Cen,

Hongyi Lin

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(20)

Published: June 27, 2024

Abstract Herein, a method for the assembly of biologically valuable 3‐selenospiro[4,5]decatrienones through CuBr 2 ‐catalyzed ispo ‐cyclization Se powder, boronic acids, and N ‐( p ‐methoxyaryl)propiolamides has been established. In this protocol, noble transition metal, prefunctionalized selenylation reagent, strong chemical oxidant are not employed. This feature wide substrate scope, good functional group tolerance, easy operation, employing earth‐abundant metal as catalyst green air oxidant. Furthermore, several derivatizations performed to showcase practicability our strategy.

Language: Английский

Citations

1
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

1