Organo-photoredox-Catalyzed Atom-Transfer Radical Substitution of Alkenes with α-Carbonyl Alkyl Halides

2020 ◽  
Vol 22 (22) ◽  
pp. 8952-8956
Author(s):  
Goki Hirata ◽  
Taisei Shimada ◽  
Takashi Nishikata
Keyword(s):  
Alkyl Halides ◽  
Atom Transfer ◽  
Radical Substitution

Photoredox Polyfluoroarylation of Alkyl Halides via Halogen Atom Transfer

2022 ◽  
Author(s):  
Ben Niu ◽  
Krishnakumar Sachidanandan ◽  
Bryan G. Blackburn ◽  
Maria Victoria Cooke ◽  
Sébastien Laulhé
Keyword(s):  
Halogen Atom ◽  
Alkyl Halides ◽  
Atom Transfer

Atom Transfer Polymerization of Methyl Methacrylate Mediated by Alkylpyridylmethanimine Type Ligands, Copper(I) Bromide, and Alkyl Halides in Hydrocarbon Solution

1999 ◽  
Vol 32 (7) ◽  
pp. 2110-2119 ◽  
Author(s):  
David M. Haddleton ◽  
Martin C. Crossman ◽  
Bogdan H. Dana ◽  
David J. Duncalf ◽  
Alex M. Heming ◽  
...  
Keyword(s):  
Methyl Methacrylate ◽  
Alkyl Halides ◽  
Atom Transfer ◽  
Hydrocarbon Solution

Alkylation of the dimethylglyoximato ligands in reduced cobaloxime

1976 ◽  
Vol 54 (9) ◽  
pp. 1425-1427 ◽  
Author(s):  
Richard B. Silverman ◽  
D. Dolphin
Keyword(s):  
Methyl Ether ◽  
Alkyl Halides ◽  
Transfer Reactions ◽  
Atom Transfer ◽  
Atom Transfer Reactions

Cobalt(II) cobaloximes can undergo atom transfer reactions with certain alkyl halides to give the corresponding alkyl cobalt(III) cobaloximes. However, in the presence of powerfully electrophilic alkyl halides, such as chloromethyl methyl ether, reaction at the periphery, and not at the cobalt, occurs to give dimethylglyoxime-O-methoxymethyl ether.

In Situ Generation of Radical Initiators: Air Stable Amine-Borane Complexes Promote Atom Transfer Radical Additions of Alkyl Halides to Alkenes

2020 ◽  
Author(s):  
Virginie Liautard ◽  
Marine Delgado ◽  
Boris Colin ◽  
Laurent Chabaud ◽  
Guillaume Michaud ◽  
...  
Keyword(s):  
Molecular Level ◽  
Radical Cyclization ◽  
Alkyl Halides ◽  
Atom Transfer ◽  
Organic Transformations ◽  
Radical Intermediate ◽  
Radical Chain ◽  
Initiation Step ◽  
Radical Initiators

Despite their instability, carbon-centered radicals have been involved as intermediates in many organic transformations that are essential to mankind. Radical polymerization,1-5 for example, provides a large part of polyacrylates and polystyrenes used as commodities in our everyday life. On a molecular level, the outcome of radical-mediated reactions is usually very different from those obtained via classical ionic based organic reactions. This is known since the 1930’s6 and has witnessed extensive developments such as radical cyclization or Atom Transfer Radical Additions (ATRA)7-9 . Radical processes10 typically begin with an initiation step in which the first radical species is created. It is eventually followed by one or several transfer steps which ultimately conduct to the formation of the main radical intermediate responsible for the reaction. The propagation steps of the radical chain are a succession of radical based transformations which, combined, outline the expected transformation.

Hydroalkylation of Olefins to form Quaternary Carbons

2019 ◽  
Author(s):  
Samantha Green ◽  
Tucker R. Huffman ◽  
Ruairí McCourt ◽  
Vincent van der Puyl ◽  
Ryan Shenvi
Keyword(s):  
Hydrogen Atom ◽  
Catalytic System ◽  
Metal Hydride ◽  
Hydrogen Atom Transfer ◽  
Alkyl Halides ◽  
Atom Transfer ◽  
Hydride Hydrogen ◽  
Radical Traps ◽  
Quaternary Carbons

Metal-hydride hydrogen atom transfer (MHAT) functionalizes unbiased alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp<sup>3 </sup>electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that allows for the hydroalkylation of unactivated olefins by unactivated alkyl halides, yielding aliphatic quaternary carbons.

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