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

scholarly journals Regio- and chemoselective Csp3–H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis

2018 ◽  
Vol 9 (44) ◽  
pp. 8453-8460 ◽  
Author(s):  
Takafumi Ide ◽  
Joshua P. Barham ◽  
Masashi Fujita ◽  
Yuji Kawato ◽  
Hiromichi Egami ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Single Electron ◽  
Atom Transfer ◽  
Single Electron Transfer ◽  
Synergistic Catalysis

Catalyst controlled regio-, and chemo-selective C-H arylation of benzylamines.

scholarly journals Cytochrome P450-catalyzed dealkylation of atrazine byRhodococcussp. strain NI86/21 involves hydrogen atom transfer rather than single electron transfer

2014 ◽  
Vol 43 (32) ◽  
pp. 12175-12186 ◽  
Author(s):  
Armin H. Meyer ◽  
Agnieszka Dybala-Defratyka ◽  
Peter J. Alaimo ◽  
Inacrist Geronimo ◽  
Ariana D. Sanchez ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Cytochrome P450 ◽  
Hydrogen Atom ◽  
Isotope Effects ◽  
Hydrogen Atom Transfer ◽  
Single Electron ◽  
Atom Transfer ◽  
Single Electron Transfer ◽  
Position Specificity

Isotope effects and position-specificity of hydroxylation pinpoint hydrogen atom transfer (HAT) as prevailing mechanism in P450 catalyzed N-dealkylation of atrazine.

Nature of transients produced on hydrogen atom transfer from capsaicin

2018 ◽  
Vol 17 (05) ◽  
pp. 1850036
Author(s):  
Ravi Joshi
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom ◽  
Dissociation Energy ◽  
Density Functional ◽  
Hydrogen Atom Transfer ◽  
Single Electron ◽  
Basis Set ◽  
Atom Transfer ◽  
Field Calculation ◽  
Single Electron Transfer

Structure and energies of capsaicin and its probable transients formed in oxidation processes (single electron transfer and hydrogen atom transfer) have been investigated using theoretical calculations. Molecular geometries and energies of truncated and complete capsaicin structures have been optimized using density functional theory (DFT) with Becke three-parameter Lee-Yang-Parr (B3LYP) functional and 6–31[Formula: see text]G(d) basis set. The stable geometries have been confirmed by vibrational analysis. The calculations suggest that single-electron transfer takes place at phenolic O-atom in the first step followed by delocalization of positive charge over the whole molecule. Further, the first step of hydrogen atom abstraction should take place at phenolic group due to lowest dissociation energy but post-optimization bond dissociation energy is least for benzylic group in the side chain as compared to other transients. Effect of water as a solvent on the energies has also been studied using self-consistent reaction field calculation. Similar results are obtained for truncated and complete capsaicin structures. The present study also includes Mulliken spin, charge, vibrational frequencies and assignments of frequencies of the transients. The present study provides explanation for the observation of phenoxyl radical in fast kinetic studies using pulse radiolysis study and, formation of breakdown and dimeric products in other studies.

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.

scholarly journals Defining a standardized methodology for the determination of the antioxidant capacity: case study of Pistacia atlantica leaves

The Analyst ◽  
2020 ◽  
Vol 145 (2) ◽  
pp. 557-571 ◽  
Author(s):  
Ziyad Ben Ahmed ◽  
Yousfi Mohamed ◽  
Viaene Johan ◽  
Bieke Dejaegher ◽  
Kristiaan Demeyer ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Electron Transfer ◽  
Hydrogen Atom ◽  
Antioxidant Capacity ◽  
Hydrogen Atom Transfer ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Pistacia Atlantica

Antioxidant activity can be measured by a variety of methods, that include hydrogen atom transfer (HAT) and single electron transfer (ET) methods.

ChemInform Abstract: Transition-Metal-Free Cross-Coupling Reactions by Single Electron Transfer (SET).

ChemInform ◽  
2014 ◽  
Vol 45 (42) ◽  
pp. no-no
Author(s):  
Suresh Kumar Sythana ◽  
Santhosh Unni ◽  
Yogesh M. Kshirsagar ◽  
Pundlik R. Bhagat
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Cross Coupling ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Coupling Reactions ◽  
Metal Free ◽  
Cross Coupling Reactions

Transition-Metal-Free Cross-Coupling Reactions by Single Electron Transfer (SET)

2013 ◽  
Vol 2014 (2) ◽  
pp. 311-314 ◽  
Author(s):  
Suresh Kumar Sythana ◽  
Santhosh Unni ◽  
Yogesh M. Kshirsagar ◽  
Pundlik R. Bhagat
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Cross Coupling ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Coupling Reactions ◽  
Metal Free ◽  
Cross Coupling Reactions

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>

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