Role of single electron transfer in SN2-type substitution reactions of anions with alkyl halides

1989 ◽  
Vol 54 (20) ◽  
pp. 4893-4898 ◽  
Author(s):  
F. G. Bordwell ◽  
John A. Harrelson
Keyword(s):  
Electron Transfer ◽  
Alkyl Halides ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Substitution Reactions ◽  
Type Substitution

scholarly journals Evidence of single electron transfer from the enolate anion of an N,N′-dialkyldiketopiperazine additive in BHAS coupling reactions

2017 ◽  
Vol 15 (41) ◽  
pp. 8810-8819 ◽  
Author(s):  
Katie J. Emery ◽  
Tell Tuttle ◽  
John A. Murphy
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Coupling Reactions ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Homolytic Aromatic Substitution ◽  
Enolate Anion

A designed N,N′-dialkyldiketopiperazine (DKP) provides evidence for the role of DKP additives as initiators that act by electron transfer in base-induced homolytic aromatic substitution reactions, involving coupling of haloarenes to arenes.

Evidence for single electron transfer in the reaction of alkoxides with alkyl halides

1984 ◽  
Vol 25 (45) ◽  
pp. 5107-5110 ◽  
Author(s):  
E.C. Ashby ◽  
Dong-Hak Bae ◽  
Won-Suh Park ◽  
Robert N. Depriest ◽  
Wei-Yang Su
Keyword(s):  
Electron Transfer ◽  
Alkyl Halides ◽  
Single Electron ◽  
Single Electron Transfer

scholarly journals Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1458 ◽  
Author(s):  
Kimihiro Komeyama ◽  
Ryusuke Tsunemitsu ◽  
Takuya Michiyuki ◽  
Hiroto Yoshida ◽  
Itaru Osaka
Keyword(s):  
Electron Transfer ◽  
Oxidative Addition ◽  
Alkyl Halides ◽  
Cobalt Catalysts ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Mild Conditions

A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to the homo-coupling of ubiquitous alkyl tosylates due to the high-lying σ*(C–O) orbital of the tosylates. This paper describes a Ni/Co-catalyzed protocol for the activation of alkyl tosylates on the construction of alkyl dimers under mild conditions.

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