Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents DOI Open Access
Zhu Cao,

Sun Yu-qian,

Yasu Chen

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(47)

Published: Aug. 15, 2024

Abstract Given the pivotal role of β ‐(het)arylethylamine moiety in bioactive molecules, direct amino(het)arylation alkenes occupies a privileged position construction (het)arylethylamine derivatives. Herein we devise chiral sulfoximines as novel bifunctional reagents which exhibit remarkable efficiency challenging asymmetric alkene aminohetarylation reaction, particularly terms reactivity and stereo‐control. The can be conveniently accessed gram scale, efficiently generate N ‐centered radicals under mild photochemical conditions. transformation proceeds through enantioselective 1,4‐hetaryl migration, ensuring precise chirality transfer from sulfur‐ to carbon‐centers, rendering wide applicability both aromatic aliphatic alkenes. Furthermore, method is straightforward operate does not require transition metals or photosensitizers, making it an attractive practical option.

Language: Английский

Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles DOI
Sifeng Li

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract Imidazoheterocycles have extensive applications in the pharmaceutical industry and agrochemicals. A comprehensive overview has been provided on current advancements electrochemical functionalization of imidazo‐fused heterocycles, which classified into ten different types reactions. Electrochemical synthesis emerged as a highly effective method for producing organic molecules, especially context sustainable development. Employing electrons traceless oxidant, several C−H reactions heterocycles achieved at either C3 or C5 positions. Electrons may serve reducing agent to synthesize pyridine rings that are partially fully saturated imidazo[1,2‐ ]pyridines. The purpose review is attract interest scientific community promote additional research imidazoheterocycles using methods.

Language: Английский

Citations

1
Silver-catalyzed pyrazole migration and cycloaddition reaction of diazo pyrazoleamides with ketimines DOI

Maoqing Shi,

Gejun Niu,

Tianyuan Zhang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(68), P. 10311 - 10314

Published: Jan. 1, 2023

A silver-catalyzed pyrazole migration and cycloaddition reaction was well established with high yields diastereoselectivities in a substrate-dependent fashion.

Language: Английский

Citations

3
Intramolecular trapping of spiro radicals to produce unusual cyclization products from usual migration substrates DOI Creative Commons
Jingming Zhang, Chengkou Liu,

Yaqi Qiao

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(9), P. 2461 - 2466

Published: Jan. 1, 2023

A conceptually new methodology to give unusual cyclization products from usual migration substrates was disclosed. The highly complex and structurally important valuable spirocyclic compounds were produced through radical addition, intramolecular ring opening instead of the di-functionalization olefins. Furthermore, a plausible mechanism proposed based on series mechanistic studies including trapping, clock, verification experiments intermediates, isotope labeling KIE experiments.

Language: Английский

Citations

2
Electrochemically‐Driven 1,4‐Aryl Migration via Radical Fluoromethylation of N‐Allylbenzamides: a Straightforward Access to Functionalized β‐Arylethylamines DOI Creative Commons
Étienne Derat, Géraldine Masson, Aurélie Claraz

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(29)

Published: April 30, 2024

Abstract An electrochemical radical Truce Smiles rearrangement of N‐allylbenzamides is documented herein. The selective 1,4‐aryl migration was triggered by the fluoromethylation alkene providing a direct route to fluoro derivatives highly privileged β‐arylethylamine pharmacophore. This practical transformation utilizes readily available starting materials and employs an electrical current drive oxidative process under mild reaction conditions. It accommodates variety migratory aryl groups with different electronic properties substitution patterns. Careful selection protecting group on nitrogen atom N‐allylbenzamide crucial outcompete undesired 6‐ endo cyclization achieve high level selectivity towards migration. DFT calculations support mechanism unveil origin between two competitive pathways.

Language: Английский

Citations

0
Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents DOI Open Access
Zhu Cao,

Sun Yu-qian,

Yasu Chen

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(47)

Published: Aug. 15, 2024

Abstract Given the pivotal role of β ‐(het)arylethylamine moiety in bioactive molecules, direct amino(het)arylation alkenes occupies a privileged position construction (het)arylethylamine derivatives. Herein we devise chiral sulfoximines as novel bifunctional reagents which exhibit remarkable efficiency challenging asymmetric alkene aminohetarylation reaction, particularly terms reactivity and stereo‐control. The can be conveniently accessed gram scale, efficiently generate N ‐centered radicals under mild photochemical conditions. transformation proceeds through enantioselective 1,4‐hetaryl migration, ensuring precise chirality transfer from sulfur‐ to carbon‐centers, rendering wide applicability both aromatic aliphatic alkenes. Furthermore, method is straightforward operate does not require transition metals or photosensitizers, making it an attractive practical option.

Language: Английский

Citations

0