Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone DOI
Xinyu Zhu, Chen Bao, Xingxian Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through radical difunctionalization alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis an open-flask atmosphere, the reaction highlighted with good yields broad scope. Mechanism studies show that initiated by formal [4 + 2] cyclization sulfonyl in regioselective manner.

Language: Английский

Iron-catalyzed direct N-methylation of N-methoxy benzamides: A solvent-free approach to bisamides utilizing the methoxy group as a “build-in” methylene donor DOI
Dandan Jiang, Jun Xiao,

Lai-Xi Zou

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141472 - 141472

Published: Jan. 1, 2025

Language: Английский

Citations

0
Mechanistic and Computational Insights into Asymmetric Intramolecular Iron-Catalyzed Nitrene Transfer into Benzylic C–H Bonds DOI
Kyeongdeok Seo, Yu Zhang, Tuấn Anh Trịnh

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3789 - 3798

Published: Feb. 18, 2025

Language: Английский

Citations

0
Tailoring C–H amination activity via modification of the triazole-derived carbene ligand DOI Creative Commons
Luke A. Hudson, Wowa Stroek, Martin Albrecht

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(35), P. 14795 - 14800

Published: Jan. 1, 2024

Two new C,O-bidentate chelating triazolylidene-phenolate ligands were synthesized that feature a diisopropylphenyl (dipp) and an adamantyl (Ad) substituent respectively on the triazole scaffold. Subsequent metalation afforded iron(II) complexes [Fe(C^O)

Language: Английский

Citations

2
Mechanochemical Conditions for Intramolecular N–O Couplings via Rhodium Nitrenoids Generated from N‐Acyl Sulfonimidamides DOI Creative Commons

Shulei Pan,

Peng Wu,

Dimitra Bampi

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 9, 2024

Abstract Starting from N ‐acyl sulfonimidamides, mechanochemically generated rhodium nitrenoids undergo intramolecular N−O couplings to provide unprecedented 1,3,2,4‐oxathiadiazole 3‐oxides in good excellent yields. The cyclization proceeds efficiently with a catalyst loading of only 0.5 mol % the presence phenyliodine(III) diacetate (PIDA) as oxidant. Neither an inert atmosphere nor additional heating is required this solvent‐free procedure. Under heat or blue light, newly formed five‐membered heterocycles function nitrene precursors reacting sulfoxides exemplified by imidation dimethyl sulfoxide.

Language: Английский

Citations

2
Mechanochemical Conditions for Intramolecular N–O Couplings via Rhodium Nitrenoids Generated from N‐Acyl Sulfonimidamides DOI Creative Commons

Shulei Pan,

Peng Wu,

Dimitra Bampi

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 9, 2024

Abstract Starting from N ‐acyl sulfonimidamides, mechanochemically generated rhodium nitrenoids undergo intramolecular N−O couplings to provide unprecedented 1,3,2,4‐oxathiadiazole 3‐oxides in good excellent yields. The cyclization proceeds efficiently with a catalyst loading of only 0.5 mol % the presence phenyliodine(III) diacetate (PIDA) as oxidant. Neither an inert atmosphere nor additional heating is required this solvent‐free procedure. Under heat or blue light, newly formed five‐membered heterocycles function nitrene precursors reacting sulfoxides exemplified by imidation dimethyl sulfoxide.

Language: Английский

Citations

0
Fe‐Catalyzed α‐C(sp3)–H Amination of N‐Heterocycles DOI Creative Commons
Andrea Geraci, Olivier Baudoin

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 16, 2024

Abstract Nitrogen‐heterocycles are privileged structures in both marketed drugs and natural products. On the other hand, C−H amination reactions furnish unconventional straightforward approaches for construction of C−N bonds. Yet, most known methods rely on precious metal catalysts. Herein we report a site‐selective intermolecular C(sp 3 )−H N‐heterocycles, catalyzed by inexpensive FeCl 2, which allows functionalization wide range pharmaceutically relevant cyclic amines. The occurs site‐selectively α‐position to nitrogen atom, even when weaker bonds present, furnishes Troc‐protected aminals or amidines. method employs N‐heterocycle as limiting reagent is applicable late‐stage complex molecules. Its synthetic potential was further illustrated through derivatization α‐aminated products application concise total synthesis reported structure senobtusin. Mechanistic studies allowed propose plausible reaction mechanism involving turnover‐limiting Fe‐nitrene generation followed fast H atom transfer radical rebound.

Language: Английский

Citations

0
Fe‐Catalyzed α‐C(sp3)–H Amination of N‐Heterocycles DOI Creative Commons
Andrea Geraci, Olivier Baudoin

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 16, 2024

Abstract Nitrogen‐heterocycles are privileged structures in both marketed drugs and natural products. On the other hand, C−H amination reactions furnish unconventional straightforward approaches for construction of C−N bonds. Yet, most known methods rely on precious metal catalysts. Herein we report a site‐selective intermolecular C(sp 3 )−H N‐heterocycles, catalyzed by inexpensive FeCl 2, which allows functionalization wide range pharmaceutically relevant cyclic amines. The occurs site‐selectively α‐position to nitrogen atom, even when weaker bonds present, furnishes Troc‐protected aminals or amidines. method employs N‐heterocycle as limiting reagent is applicable late‐stage complex molecules. Its synthetic potential was further illustrated through derivatization α‐aminated products application concise total synthesis reported structure senobtusin. Mechanistic studies allowed propose plausible reaction mechanism involving turnover‐limiting Fe‐nitrene generation followed fast H atom transfer radical rebound.

Language: Английский

Citations

0
Iron-catalysed intramolecular C(sp3)–H amination of alkyl azides DOI Creative Commons
Kai Wu, Chi‐Ming Che

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(95), P. 13998 - 14011

Published: Jan. 1, 2024

Iron-catalysed intramolecular C(sp

Language: Английский

Citations

0
Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone DOI
Xinyu Zhu, Chen Bao, Xingxian Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through radical difunctionalization alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis an open-flask atmosphere, the reaction highlighted with good yields broad scope. Mechanism studies show that initiated by formal [4 + 2] cyclization sulfonyl in regioselective manner.

Language: Английский

Citations

0