Regio- and Stereoselective Electro-Mediated Carboalkoxylation of 1,3-Dienes DOI

Ophélie Montiège,

Marion Siccardi,

Morgane Sanselme

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(51), P. 11105 - 11110

Published: Dec. 16, 2024

1,3-Dienes are versatile raw materials for building molecular complexity. We report herein mild conditions the regio- and stereoselective [only (E) isomer obtained] 1,4-carboalkoxylation of 1,3-dienes. This electrochemical multicomponent reaction provides an eco-efficient straightforward access to a diverse range (E)-polyfunctionalized allyl ether products, without requiring any metal catalyst.

Language: Английский

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

Citations

15

Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes DOI

Kaixing Gong,

Yingchun Ma,

Ping Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2352 - 2362

Published: April 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Language: Английский

Citations

9

Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide DOI

Dongyin Wang,

Li Zeng, Jifu Shi

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

Citations

6

Metabolic Engineering of Escherichia coli for the Improved Malonic Acid Production DOI
Han Liu,

Mengzhen Tian,

Pingsha Dong

et al.

ACS Synthetic Biology, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Malonic acid (MA) is a high-value chemical with diverse applications in the fields of food, agriculture, medicine, and synthesis. Despite successful biosynthesis MA has been performed Escherichia coli, Myceliophthora thermophila, Saccharomyces cerevisiae, resulting titers remain insufficient for industrial-scale production. In this study, three distinct metabolic pathways were designed constructed to increase production E. coli. Among these, fumaric pathway comprising four key enzymes including aspartase (AspA), decarboxylase (PanD), β-alanine-pyruvate transaminase (Pa0132), succinic aldehyde dehydrogenase (YneI) was identified as most effective Additionally, supplementation found significantly improve To further enhance production, engineering strategies employed, deletion ydfG gene, responsible encoding malonic semialdehyde reductase, ptsG which encodes glucose transporter. Finally, through optimization fermentation conditions feeding strategies, engineered strain achieved an titer 1.4 g/L shake flask 17.8 fed-batch fermentation. This study provides new insights into utilizing metabolically coli cells.

Language: Английский

Citations

0

Cascade Cyclization of N-Cyanamide Alkenes for the Divergent Synthesis of Azido-, Nitro-, and Alkenyl-Containing Pyrroloquinazolinones DOI
Bo Jiang, Cui Zhang,

Tai‐Gang Fan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8028 - 8033

Published: Sept. 16, 2024

Radical cascade cyclizations of

Citations

2

Acid-catalyzed radical tandem alkylation/cyclization of unactivated alkenes with ketones: Access to ketoalkyl-substituted quinazolinone derivatives DOI

Jian-Li Wu,

Meng Yan,

Lulu Fan

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 162, P. 134085 - 134085

Published: June 11, 2024

Language: Английский

Citations

2

Photoelectrochemical synthesis of 4-halomethyl benzoxazines with a halogen anion source DOI
Xiang Chen,

Xiao Li,

Hui Dai

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5553 - 5557

Published: Jan. 1, 2024

A mild and efficient protocol for preparing 4-halomethyl benzoxazines via a photoelectrochemical process with ammonium halide as the halogenating reagent was developed.

Language: Английский

Citations

2

Visible-light promoted radical cascade cyclization of 3-allyl-2-arylquinazolinones for the synthesis of phosphorylated dihydroisoquinolino[1,2-b]quinazolinones DOI
Jun Huang,

Caijin Ban,

J. J. Qin

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8119 - 8122

Published: Jan. 1, 2024

A novel visible-light promoted metal-free radical cascade cyclization reaction has been developed with 3-allyl-2-arylquinazolinones as a new class of acceptor. This photocatalytic protocol represents an efficient approach to construct phosphorylated dihydroisoquinolino[1,2-

Language: Английский

Citations

1

Electrochemical 1,5-chlorosulfonylation and 1,5-hydrosulfonylation of vinylcyclopropanes DOI
Xin Zhang, Wei Li,

Yuxiang Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5564 - 5572

Published: Jan. 1, 2024

This study reports the electrochemical reaction of vinylcyclopropanes with sulfonyl chlorides, resulting in 1,5-hydrosulfonylation and 1,5-chlorosulfonylation.

Language: Английский

Citations

1

Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones DOI
Dong Li,

Xiaoqing Wang,

Yanhui Gou

et al.

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

Published: Oct. 2, 2024

New photochemical approaches to 2,3-fused quinazolinones and dihydroquinazolinones are disclosed. The intramolecular hydrocyclization proceeds in moderate excellent yields across diverse alkenes with high regioselectivity diastereocontrol. Mechanistic studies indicated that the radical cascade processes involve thiophenol acting as single-electron transfer hydrogen atom reagents. success of gram-scale synthesis proves strategy can be used for practical applications.

Language: Английский

Citations

1