One-Pot Sequential Azide-Alkyne [3+2] Cycloaddition and Atom Transfer Radical Addition (ATRA): Expanding the Scope of In Situ Copper(I) Regeneration in the Presence of Environmentally Benign Reducing Agent

2011 ◽  
Vol 2011 (8) ◽  
pp. 1292-1301 ◽  
Author(s):  
Carolynne L. Ricardo ◽  
Tomislav Pintauer
Keyword(s):  
Radical Addition ◽  
Reducing Agent ◽  
Environmentally Benign ◽  
Atom Transfer ◽  
One Pot ◽  
Atom Transfer Radical Addition

Highly Efficient Ambient-Temperature Copper-Catalyzed Atom-Transfer Radical Addition (ATRA) in the Presence of Free-Radical Initiator (V-70) as a Reducing Agent

2009 ◽  
Vol 15 (1) ◽  
pp. 38-41 ◽  
Author(s):  
Tomislav Pintauer ◽  
William T. Eckenhoff ◽  
Carolynne Ricardo ◽  
Marielle N. C. Balili ◽  
Ashley B. Biernesser ◽  
...  
Keyword(s):  
Free Radical ◽  
Ambient Temperature ◽  
Radical Addition ◽  
Reducing Agent ◽  
Atom Transfer ◽  
Radical Initiator ◽  
Highly Efficient ◽  
Atom Transfer Radical Addition ◽  
Free Radical Initiator

scholarly journals Cyclopropanation of Terminal Alkenes via Sequential Atom Transfer Radical Addition – 1,3-Elimination

2019 ◽  
Author(s):  
Nicholas D. C. Tappin ◽  
Weronika Michalska ◽  
Simon Rohrbach ◽  
Philippe Renaud
Keyword(s):  
Ethyl Acetate ◽  
Radical Addition ◽  
Atom Transfer ◽  
Reaction Sequence ◽  
One Pot ◽  
Tetrabutylammonium Fluoride ◽  
Wide Range ◽  
Atom Transfer Radical Addition ◽  
Simple Protocol ◽  
Terminal Alkenes

An operationally simple protocol to affect an atom transfer radical addition (ATRA) of commercially available ICH<sub>2</sub>Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with tetrabutylammonium fluoride (TBAF). This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated. The whole reaction sequence relies on simple reagents such dilauroyl peroxide (DLP) and TBAF and can be run on multi-gram scales in ethyl acetate as a solvent.

Cyclopropanation of Terminal Alkenes via Sequential Atom Transfer Radical Addition – 1,3-Elimination

2019 ◽  
Author(s):  
Nicholas D. C. Tappin ◽  
Weronika Michalska ◽  
Simon Rohrbach ◽  
Philippe Renaud
Keyword(s):  
Ethyl Acetate ◽  
Radical Addition ◽  
Atom Transfer ◽  
Reaction Sequence ◽  
One Pot ◽  
Tetrabutylammonium Fluoride ◽  
Wide Range ◽  
Atom Transfer Radical Addition ◽  
Simple Protocol ◽  
Terminal Alkenes

An operationally simple protocol to affect an atom transfer radical addition (ATRA) of commercially available ICH<sub>2</sub>Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with tetrabutylammonium fluoride (TBAF). This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated. The whole reaction sequence relies on simple reagents such dilauroyl peroxide (DLP) and TBAF and can be run on multi-gram scales in ethyl acetate as a solvent.

Atom-transfer radical addition of fluoroalkyl bromides to alkenes via a photoredox/copper catalytic system

2021 ◽  
Author(s):  
Vladislav S. Kostromitin ◽  
Artem A. Zemtsov ◽  
Vladimir A. Kokorekin ◽  
Vitalij V. Levin ◽  
Alexander D. Dilman
Keyword(s):  
Catalytic System ◽  
Radical Addition ◽  
Atom Transfer ◽  
Alkyl Bromides ◽  
System P ◽  
Atom Transfer Radical Addition

A method for the addition of fluorinated alkyl bromides to alkenes is described.

ChemInform Abstract: Regioisomerized Atom Transfer Radical Addition (ATRA) of Olefins with Dichlorofluorocarbons.

ChemInform ◽  
2016 ◽  
Vol 47 (16) ◽  
Author(s):  
Bo Zhao ◽  
Ju-You Lu ◽  
Yang Li ◽  
Dong-Huai Tu ◽  
Zhao-Tie Liu ◽  
...  
Keyword(s):  
Radical Addition ◽  
Atom Transfer ◽  
Atom Transfer Radical Addition
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