The Merger of Photocatalyzed Hydrogen Atom Transfer with Transition Metal Catalysis for C‐H Functionalization of Alkanes and Cycloalkanes

2021 ◽  
Author(s):  
Ziqi Ye ◽  
Yu-Mei Lin ◽  
Lei Gong
Keyword(s):  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Transition Metal Catalysis ◽  
Atom Transfer ◽  
Metal Catalysis

Direct Cyclization of Alkenyl Thioester via Transition Metal‐hydrogen Atom Transfer/radical‐polar Crossover Mechanism

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Synthetic Method ◽  
Atom Transfer ◽  
Reaction Conditions ◽  
Hydride Hydrogen ◽  
Sulfur Heterocycles ◽  
One Step

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>

scholarly journals Trends in Ground-State Entropies for Transition Metal Based Hydrogen Atom Transfer Reactions

2009 ◽  
Vol 131 (12) ◽  
pp. 4335-4345 ◽  
Author(s):  
Elizabeth A. Mader ◽  
Virginia W. Manner ◽  
Todd F. Markle ◽  
Adam Wu ◽  
James A. Franz ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Transition Metal ◽  
Ground State ◽  
Hydrogen Atom Transfer ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions

Transition-metal-free radical relay cyclization of vinyl azides with 1,4-dihydropyridines involving a 1,5-hydrogen-atom transfer: access to α-tetralone scaffolds

2020 ◽  
Vol 7 (22) ◽  
pp. 3638-3647
Author(s):  
Yangzhen Liao ◽  
Yu Ran ◽  
Guijun Liu ◽  
Peijun Liu ◽  
Xiaozu Liu
Keyword(s):  
Free Radical ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Metal Free ◽  
Vinyl Azides

The remote C(sp3)–H functionalization enabled by a radical-mediated 1,5-hydrogen-atom transfer (HAT) process using vinyl azides and 1,4-dihydropyridines as precursors has been described.

Direct Cyclization of Alkenyl Thioester via Transition Metal‐hydrogen Atom Transfer/radical‐polar Crossover Mechanism

2019 ◽  
Author(s):  
Shiori Date ◽  
Kensei Hamasaki ◽  
Karen Sunagawa ◽  
Hiroki Koyama ◽  
Chikayoshi Sebe ◽  
...  
Keyword(s):  
Natural Products ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Synthetic Method ◽  
Atom Transfer ◽  
Reaction Conditions ◽  
Hydride Hydrogen ◽  
Sulfur Heterocycles ◽  
One Step

<div>We report here a catalytic, Markovnikov selective, and scalable synthetic method for the synthesis of saturated sulfur heterocycles, which are found in the structures of pharmaceuticals and natural products, in one step from an alkenyl thioester. Unlike a potentially labile alkenyl thiol, an alkenyl thioester is stable and easy to prepare. The powerful Co catalysis via a cobalt hydride hydrogen atom transfer and radical-polar crossover mechanism enabled simultaneous cyclization and deprotection. The substrate scope was expanded by the extensive optimization of the reaction conditions and tuning of the thioester unit.</div>

Organocatalytic Atom-Transfer C(sp3)–H Oxidation

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2331-2336 ◽  
Author(s):  
Michael Hilinski ◽  
Shea Johnson ◽  
Logan Combee
Keyword(s):  
Transition Metal ◽  
Late Stage ◽  
Transition Metal Catalysis ◽  
Great Promise ◽  
Atom Transfer ◽  
Complex Molecules ◽  
Metal Catalysis ◽  
Iminium Salt ◽  
Site Selective

Predictably site-selective catalytic methods for intermolecular C(sp3)–H hydroxylation and amination hold great promise for the synthesis and late-stage modification of complex molecules. Transition-metal catalysis has been the most common approach for early investigations of this type of reaction. In comparison, there are far fewer ­reports of organocatalytic methods for direct oxygen or nitrogen insertion into C–H bonds. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of an iminium salt that catalyzes both oxygen and nitrogen insertion.1 Introduction2 Background: C–H Oxidation Capabilities of Heterocyclic Oxidants3 Oxaziridine-Mediated Catalytic Hydroxylation4 Dioxirane-Mediated Catalytic Hydroxylation5 Iminium Salt Catalysis of Hydroxylation and Amination6 Conclusion and Outlook

Transition-Metal-Free C(sp3)–H Coupling of Cycloalkanes Enabled by Single-Electron Transfer and Hydrogen Atom Transfer

2021 ◽  
Vol 23 (5) ◽  
pp. 1714-1719
Author(s):  
Linlin Zhang ◽  
Zhengfen Liu ◽  
Xun Tian ◽  
Yujin Zi ◽  
Shengzu Duan ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom ◽  
Transition Metal ◽  
Hydrogen Atom Transfer ◽  
Single Electron ◽  
Atom Transfer ◽  
Single Electron Transfer ◽  
Metal Free
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