DigiChemTree enables programmable light-induced carbene generation for on demand chemical synthesis DOI Creative Commons
Abhilash Rana, Ruchi Chauhan,

Amirreza Mottafegh

et al.

Communications Chemistry, Journal Year: 2024, Volume and Issue: 7(1)

Published: Nov. 1, 2024

The reproducibility of chemical reactions, when obtaining protocols from literature or databases, is highly challenging for academicians, industry professionals and even now the machine learning process. To synthesize organic molecule under photochemical condition, several years reaction optimization, skilled manpower, long time etc. are needed, resulting in non-affordability slow down research development. Herein, we have introduced DigiChemTree backed with artificial intelligence to auto-optimize parameter synthesizing on demand library molecules fast manner. Newly, auto-generated digital code was further tested late stage functionalization various active pharmaceutical ingredient.

Language: Английский

Electrochemical radical-polar crossover: a radical approach to polar chemistry DOI

Zhoumei Tan,

Haonan Zhang, Kun Xu

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 450 - 470

Published: Nov. 3, 2023

Language: Английский

Citations

50

Electrochemical generation and utilization of radical intermediates DOI

Zhong‐Wei Hou,

Hai‐Chao Xu, Lei Wang

et al.

Current Opinion in Electrochemistry, Journal Year: 2024, Volume and Issue: 44, P. 101447 - 101447

Published: Jan. 26, 2024

Language: Английский

Citations

20

Photodriven Radical-Polar Crossover Cyclization Strategy: Synthesis of Pyrazolo[1,5-a]pyridines from Diazo Compounds DOI
Peng Zhao, Yanbo Liu, Yuting Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2511 - 2516

Published: March 20, 2024

This work demonstrates the synthesis of a variety perfluoroalkyl heterocycles via visible-light-driven radical-polar crossover cyclization strategy. In this process, single-electron reduction/SNV-type/cyclization sequences follow radical addition reaction diazoester, which differs from current role diazoesters as precursors/acceptors. transformation excellent functional group compatibility and allows for modification many bioactive molecules with diazoesters. Such could represent novel approach to photochemical diazo compounds.

Language: Английский

Citations

18

Silver-Promoted Three-Component Synthesis of Perfluoroalkenyl Pyrroles through Partial Defluorinative Functionalization of Perfluoroalkyl Halides DOI
Wenjun Ji, Wei Han,

Yuanyuan Ren

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6197 - 6202

Published: July 15, 2024

A silver-promoted three-component heterocyclization of alkynes, perfluoroalkyl halides, and 1,3-dinucleophiles was developed for the efficient synthesis privileged (E)-perfluoroalkenyl pyrroles. The reaction proceeded through a rationally designed sequence radical perfluoroalkylation intramolecular defluorinative [3 + 2]-heterocyclization. utility halide as perfluoroalkenyl reagent, by selective controllable functionalization two inert C(sp3)–F bonds at vicinal carbon centers on chain, provides new mode value-added organofluorides starting from easily available low-cost fluorinated feedstock.

Language: Английский

Citations

11

Skeletal Editing: Ring Insertion for Direct Access to Heterocycles DOI Creative Commons

Xue Li,

Zhigang Xu

Molecules, Journal Year: 2024, Volume and Issue: 29(9), P. 1920 - 1920

Published: April 23, 2024

Skeleton editing has rapidly advanced as a synthetic methodology in recent years, significantly streamlining the synthesis process and gaining widespread acceptance drug development. This field encompasses diverse ring reactions, many of which exhibit immense potential skeleton editing, facilitating generation novel skeletons. Notably, reactions that involve cleavage two distinct rings followed by reformation new through insertion play pivotal role construction article aims to compile systematize this category emphasizing primary reaction types offering thorough exploration their associated complexities challenges. Our endeavor is furnish readers with comprehensive strategies, igniting research interest injecting fresh impetus into advancement domain.

Language: Английский

Citations

6

Highly regioselective electrochemical oxidative 2,1-azolization of alkenes with azoles and nucleophiles DOI
Yaqi Deng, Jian Xue, Xiang Wu

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110822 - 110822

Published: Jan. 1, 2025

Language: Английский

Citations

0

Exploring Diazo Compounds for the Divergent Electro-Cascade Sequence and S–H Insertion Reaction DOI
Jaswant Kumar, Deepak Sharma, Yaseen Hussain

et al.

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

Published: Feb. 12, 2025

We have explored the reactivity of diazo compounds under electrochemical conditions to establish a cascade sequence thiolation/cyclization/reduction reactions. Electrolyzing styryl imides and aryl thiols enables direct access single diastereoisomer 2,5-pyrrolidine-dione-fused thiochromans in good yield mild metal-free conditions. Notably, tunable has been achieved via S–H insertion at center modified reaction Based on experimental evidences, including detection key intermediates computational studies, mechanism for also established.

Language: Английский

Citations

0

Dimethoxyacetaldehyde-N-triftosylhydrazone: Preparation and Carbene Reactivity in Cyclopropanation and Doyle–Kirmse Reactions DOI
Yifan Zhang, Shuang Li, Hongzhu Chen

et al.

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

Published: Feb. 20, 2025

Herein, we developed the new, powerful, and easy-to-handle chemical reagent, dimethoxyacetaldehyde-N-triftosylhydrazone (DMHz-Tfs), as a convenient in situ source of dimethoxydiazoethane under mild conditions. We demonstrate carbene reactivity DMHz-Tfs iron-catalyzed cyclopropanation Doyle-Kirmse reactions, providing access to diverse acetal functionalized cyclopropanes homoallylic- allenyl-sulfides at gram-scale with high stereoselectivity. DFT calculations elucidated involvement most stable doublet spin state iron-carbene intermediate over other possible states.

Language: Английский

Citations

0

Photoelectrocatalytic Cl-mediated C(sp3)–H aminomethylation of hydrocarbons by BiVO4 photoanodes DOI Creative Commons

Anzai Shi,

Pengfei Xie, Yanwei Wang

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 8, 2025

Interfacial photoelectrochemistry at photoanodes has been extensively researched for solar energy conversion, but its application the production of high-value-added chemical compounds in organic chemistry still presents challenges. Herein, we report photoelectrocatalytic Cl-mediated C(sp3)–H aminomethylation alkanes with self-developed and reusable BiVO4 photoanodes. The swift condensation aniline aldehydes, along decrease electricity input by photogenerated holes photoanodes, work together to prevent excessive oxidation aniline, leading high yields desired product. Mechanistic experiments demonstrate that Cl- ions, as key mediators, could be attracted oxidized form Cl2. This is followed light-promoted homolytic cleavage Cl2, generating Cl radicals efficiently abstract hydrogen atoms from hydrocarbons. opens an avenue interfacial photoelectrochemical synthesis demonstrates a potential method optimizing conversion into fuels. A stable recyclable photoelectrode material was developed efficient hydrocarbons cell, which provides promising fuel conversion.

Language: Английский

Citations

0

Photoinduced Diazo Carbene-Promoted C(sp3)–H Oxidative Cross-Coupling Reaction for α-Triazolation of Isochromans DOI
Xiao Tang, Jinhua Liu, Xiang Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 17, 2025

A photocatalytic diazo triplet carbene-promoted C(sp3)–H oxidative coupling of isochromans and triazoles was developed in up to 83% yield at room temperature air. The radical-like carbenes were used as efficient HAT acceptors, the possible synergistic enabled unprecedented process with a high regioselectivity.

Language: Английский

Citations

0