Dual-Role Disulfide-Catalyzed Intramolecular Hydroamination through N–H Activation DOI

Synfacts, Journal Year: 2023, Volume and Issue: 19(05), P. 0507 - 0507

Published: April 14, 2023

Key words N-centered radicals - disulfide catalysis pyrrolidines hydroamination

Language: Английский

Iron-Catalyzed Csp2–Csp3 Cross-Coupling via Double Decarboxylation: One Step Synthesis of Remote Polar Alkenes DOI

Ni Xiong,

Chengxiang Zhou,

Shiyi Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2029 - 2033

Published: March 4, 2024

Herein, we report an efficient photoinduced iron-catalyzed strategy for cross-couplings of alkyl carboxylic and acrylic acids, which provides a powerful tool the synthesis variety alkenes with polar functional groups. This novel synthetic methodology can also be applied to preparation ketones by using α-keto acids. Mechanistic experiments revealed preliminary mechanistic details. Diverse functionalization could achieved, may help streamline complex analogues drug discovery.

Language: Английский

Citations

7
Photoinduced Difunctionalization of Diazenes Enabled by N–N Radical Coupling DOI

Yu‐Shi Jiang,

Shanshan Li,

Xue-Ling Luo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(36), P. 6671 - 6676

Published: Aug. 29, 2023

In this study, a metal-free difunctionalization strategy for diazenes was developed using range of bifunctionalization reagents. This involves unique N(sp3)–N(sp2) radical coupling between the hydrazine and imine radical. More than 30 triazane core motifs were constructed by installing imines various functional groups, including alkyl, phenyl, cyanoalkyl, sulfonyl on both ends nitrogen–nitrogen bond in an efficient manner.

Language: Английский

Citations

17
Photoinduced Copper-Catalyzed Aminoalkylation of Amino-Pendant Olefins DOI
Cancan Zhang, Hongli Wu,

Xuan-Chi Yu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(31), P. 5862 - 5868

Published: Aug. 3, 2023

The combination of photo and copper catalysts has emerged as a novel paradigm in organic catalysis, which provides access to the acceleration chemical synthesis. Herein, we describe an aminoalkylation amino-dependent olefins with maleimides through cooperative photo/copper catalytic system. In this report, strategy allows generation broad complex functionalized nitrogenous molecules including oxazolidinones, 2-pyrrolidones, imidazolidinones, thiazolidinones, pyridines, piperidines absence external photosensitizer base. approach is achieved photoinduced Cu(I)/Cu(II)/Cu(III) species nitrogen nucleophiles, intermolecular radical addition, hydrogen atom transfer (HAT) processes. plausible mechanism investigated by series control experiments theoretical tests, scavenging experiments, deuterium labeling ultraviolet-visible absorption, cyclic voltammetry (CV) tests.

Language: Английский

Citations

14
A Type of Chiral C2-Symmetric Arylthiol Catalyst for Highly Enantioselective Anti-Markovnikov Hydroamination DOI
Lin Tang, Chaoren Shen,

Shaoyu Hao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(23), P. 16248 - 16256

Published: May 29, 2024

The development of chiral hydrogen donor catalysts is fundamental in the expansion and innovation asymmetric organocatalyzed reactions via an enantioselective atom transfer (HAT) process. Herein, unprecedented type C2-symmetric arylthiol derived from readily available enantiomeric lactate ester was developed. With these catalysts, anti-Markovnikov alkene hydroamination–cyclization reaction established, affording a variety pharmaceutically interesting 3-substituted piperidines with moderate to high enantioselectivity. Results designed control experiments theoretical computation rationalized origin stereocontrol disclosed spatial effect moiety thiols on We believed facile synthesis, flexible tunability, effective enantioselectivity-controlling capability would shed light versatile HAT related reactions.

Language: Английский

Citations

6
Integrating Olefin Carboamination and Hofmann‐Löffler‐Freytag Reaction by Radical Deconstruction of Hydrazonyl N−N Bond DOI

Si‐Pei Hu,

Chen‐Hui Gao,

Tuming Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(17)

Published: Feb. 21, 2024

As a type of elementary organic compounds containing N-N single bond, hydrazone involved chemical conversions are extremely extensive, but they mainly limited to N

Language: Английский

Citations

5
Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer DOI

Er-Meng Wang,

Ziyi Wang,

Xu Ban

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(12), P. 109843 - 109843

Published: March 29, 2024

Language: Английский

Citations

5
Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer DOI

Zhi Chen,

Wenkai Zhu,

Chaodong Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(18), P. 4709 - 4717

Published: Jan. 1, 2023

Difluorinated compounds are important structural motifs in organic synthesis and medicinal chemistry because fluoride can modulate the properties of various molecules.

Language: Английский

Citations

7
Photocatalyst-free hydrothiolation of gem-difluoroalkenes with thiols DOI

Lin Zuo,

Zhiyang Zhang,

Xiao‐Ya Yuan

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(20), P. 9000 - 9003

Published: Jan. 1, 2024

A photocatalyst-free hydrothiolation reaction of aromatic gem -difluoroalkenes was developed under the irradiation blue light in dimethyl carbonate as a green solvent.

Language: Английский

Citations

2
Photoinduced Intermolecular Hydroamination and Hydroetherification of Electron‐Rich Alkenes With Low Catalyst Loadings DOI

You‐Qin Jiang,

Pei Qu,

Yong‐Hao Wang

et al.

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(22)

Published: July 24, 2024

Abstract A photochemical method based on visible‐light irradiation (blue LEDs/sunlight) has been developed for the intermolecular hydroamination and hydroetherification of electron‐rich alkenes. This is compatible with a wide range azoles alkenes, such as vinyl ethers, sulfides enamides, performed low concentrations photocatalyst (1000 ppm). Comprehensive mechanistic studies indicate that this process initiated by formation an active radical cation intermediate through single electron oxidation azole, which mediated excited Acr‐Mes + BF 4 − .

Language: Английский

Citations

2
Visible-Light-Induced Intermolecular Trifluoromethyl Heteroarylation of Vinyl Ethers for the Syntheses of β-Trifluoromethyl Alkyl Thiochromones DOI
Shen Zhao,

Pingliang Zhu,

Baolong Xu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 9283 - 9292

Published: June 22, 2023

Herein, we reported a transition-metal-free three-component trifluoromethyl heteroarylation of vinyl ethers under visible light irradiation. This protocol proceeded through radical addition/cyclization sequence which hinged on the intrinsic nucleo/electrophilic reactivity both radicals, alkene, and alkynones, allowing β-trifluoromethyl alkyl thiochromones furnished with high efficiency excellent functional group tolerance. By virtue this procedure, three distinct chemical bonds including C(sp2)–C(sp3), C(sp3)–C(sp3), C(sp2)–S have been successively forged in single pot.

Language: Английский

Citations

5