Mn2(CO)10-catalyzed direct protic hydrogen transfer with unactivated alkenes DOI Creative Commons
Tao Li, Han Sun, Ting Shao

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 1, 2024

Language: Английский

Engaging Alkenes in Metallaphotoredox: A Triple Catalytic, Radical Sorting Approach to Olefin-Alcohol Cross-Coupling DOI
Qinyan Cai, Iona M. McWhinnie, Nathan W. Dow

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(18), P. 12300 - 12309

Published: April 24, 2024

Metallaphotoredox cross-coupling is a well-established strategy for generating clinically privileged aliphatic scaffolds via single-electron reactivity. Correspondingly, expanding metallaphotoredox to encompass new C(

Language: Английский

Citations

21
Photo‐ and Cobalt‐Catalyzed Synthesis of Heterocycles via Cycloisomerization of Unactivated Olefins DOI Creative Commons
Henry Lindner, Willi M. Amberg, Tristano C. Martini

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(19)

Published: Feb. 28, 2024

Abstract We report a general, intramolecular cycloisomerization of unactivated olefins with pendant nucleophiles. The reaction proceeds under mild conditions and tolerates ethers, esters, protected amines, acetals, pyrazoles, carbamates, arenes. It is amenable to N ‐, O as well C ‐nucleophiles, yielding number different heterocycles including, but not limited to, pyrrolidines, piperidines, oxazolidinones, lactones. Use both benzothiazinoquinoxaline organophotocatalyst Co‐salen catalyst obviates the need for stoichiometric oxidant or reductant. showcase utility protocol in late‐stage drug diversification synthesis several small natural products.

Language: Английский

Citations

19
Fe/Thiol Cooperative Hydrogen Atom Transfer Olefin Hydrogenation: Mechanistic Insights That Inform Enantioselective Catalysis DOI
Sarah R. Buzsaki, Savannah M. Mason, Padmanabha V. Kattamuri

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(25), P. 17296 - 17310

Published: June 14, 2024

Asymmetric hydrogenation of activated olefins using transition metal catalysis is a powerful tool for the synthesis complex molecules, but traditional catalysts have difficulty with enantioselective reduction electron-neutral, electron-rich, and minimally functionalized olefins. Hydrogenation based on radical, metal-catalyzed hydrogen atom transfer (mHAT) mechanisms offers an outstanding opportunity to overcome these difficulties, enabling mild challenging selectivity that complementary hydrogenations H2. Further, mHAT presents asymmetric induction through cooperative (cHAT) chiral thiols. Here, we report insights from mechanistic study iron-catalyzed achiral cHAT reaction leverage deliver stereocontrol Kinetic analysis variation silane structure point hydride iron as likely rate-limiting step. The data indicate selectivity-determining step quenching alkyl radical by thiol, which becomes more potent H donor when coordinated iron(II). resulting iron(III)–thiolate in equilibrium other species, including FeII(acac)2, shown be predominant off-cycle species. enantiodetermining nature thiol trapping enables net commercially available glucose-derived catalyst up 80:20 enantiomeric ratio. To best our knowledge, this first demonstration via mHAT. These findings advance understanding act proof principle development reactions.

Language: Английский

Citations

9
Photoinduced Co/Ni-cocatalyzed Markovnikov hydroarylation of unactivated olefins with aryl bromides DOI Creative Commons
Hongchao Liu, Xinyu Xu, Siyuan Tang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(36), P. 14865 - 14871

Published: Jan. 1, 2024

A novel photoinduced Co/Ni-cocatalyzed Markovnikov hydroarylation of unactivated alkenes with aryl bromides by using proton as a hydrogen source has been developed for the first time.

Language: Английский

Citations

4
Modifying commodity-relevant unsaturated polymers via Co-catalyzed MHAT DOI

Yun-Nian Yin,

Bang-Sen Zhao,

Han-Yuan Liu

et al.

Chem, Journal Year: 2024, Volume and Issue: 10(10), P. 3088 - 3099

Published: June 19, 2024

Language: Английский

Citations

3
Photo- and Cobalt-Catalyzed Cycloisomerization of Unsaturated Guanidines, (Iso-)Ureas, and Carbonates DOI Creative Commons
Henry Lindner, Erick M. Carreira

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

Published: Jan. 8, 2025

We report intramolecular photocatalyzed cycloisomerization of unactivated olefins with pendant nucleophiles. The reaction proceeds under mild conditions and utilizes guanidines, ureas, isoureas, isothioureas, carbonates to yield several different five-, six-, seven-membered heterocycles. Use benzothiazinoquinoxaline as an organophotocatalyst cobalt–salen catalyst obviates the need for a stoichiometric oxidant or reductant.

Language: Английский

Citations

0
Manganese-Catalyzed Mukaiyama Hydration Reaction for Undergraduate Organic Chemistry Course DOI
Nan Li, Jingyi Zhang, Beibei Ren

et al.

Journal of Chemical Education, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

Language: Английский

Citations

0
Cobalt-catalyzed radical hydroamination of olefins DOI

Qingyu Xing,

Preeti P. Chandrachud,

Khalilia Tillett

et al.

Trends in Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 1, 2025

Language: Английский

Citations

0
Cobalt-catalysed alkene hydronitration enabled by anomeric nitroamide DOI
Yu Wang, Marcell M. Bogner, Jake Bailey

et al.

Nature Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: May 21, 2025

Language: Английский

Citations

0
Catalytic hydrofunctionalizations of alkenes via hydrogen atom transfer with 3d transition metal complexes (MHAT): A pragmatic approach to recent contributions DOI Creative Commons
Antonio Torres-Calis, Juventino J. Garcı́a

Applied Catalysis A General, Journal Year: 2025, Volume and Issue: unknown, P. 120379 - 120379

Published: May 1, 2025

Language: Английский

Citations

0