Kinetic Solvent Effects on the Reactions of the Cumyloxyl Radical with Tertiary Amides. Control over the Hydrogen Atom Transfer Reactivity and Selectivity through Solvent Polarity and Hydrogen Bonding

2015 ◽  
Vol 80 (2) ◽  
pp. 1149-1154 ◽  
Author(s):  
Michela Salamone ◽  
Livia Mangiacapra ◽  
Massimo Bietti
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Atom ◽  
Solvent Effects ◽  
Solvent Polarity ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Tertiary Amides

Control of photoisomerization of CC double bond by hydrogen bonding and photoinduced hydrogen atom transfer

2007 ◽  
Vol 20 (11) ◽  
pp. 864-871 ◽  
Author(s):  
Yousuke Azechi ◽  
Keiko Takemura ◽  
Yoshihiro Shinohara ◽  
Yoshinobu Nishimura ◽  
Tatsuo Arai
Keyword(s):  
Hydrogen Bonding ◽  
Double Bond ◽  
Hydrogen Atom ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer

Solvent Effects on the Intramolecular Hydrogen-Atom Transfer between Tyrosine and Benzophenone. Diverting Reaction Mechanisms in Protic and Nonprotic Media

2009 ◽  
Vol 113 (27) ◽  
pp. 11695-11703 ◽  
Author(s):  
Gerald Hörner ◽  
Anna Lewandowska ◽  
Gordon L. Hug ◽  
Bronislaw Marciniak
Keyword(s):  
Hydrogen Atom ◽  
Solvent Effects ◽  
Reaction Mechanisms ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Intramolecular Hydrogen

scholarly journals Absolute Rate Constants for Hydrogen Atom Transfer from Tertiary Amides to the Cumyloxyl Radical: Evaluating the Role of Stereoelectronic Effects

2014 ◽  
Vol 79 (15) ◽  
pp. 7179-7184 ◽  
Author(s):  
Michela Salamone ◽  
Michela Milan ◽  
Gino A. DiLabio ◽  
Massimo Bietti
Keyword(s):  
Hydrogen Atom ◽  
Rate Constants ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Absolute Rate ◽  
Stereoelectronic Effects ◽  
Tertiary Amides

Hydrogen Atom Transfer from 1,n-Alkanediamines to the Cumyloxyl Radical. Modulating C–H Deactivation Through Acid–Base Interactions and Solvent Effects

2014 ◽  
Vol 79 (12) ◽  
pp. 5710-5716 ◽  
Author(s):  
Michela Milan ◽  
Michela Salamone ◽  
Massimo Bietti
Keyword(s):  
Hydrogen Atom ◽  
Solvent Effects ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Acid Base

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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