Bridging the Gap between Electrochemical and Organometallic Activation: Benzyl Chloride Reduction at Silver Cathodes-Reference-Cited by-同舟云学术

Bridging the Gap between Electrochemical and Organometallic Activation: Benzyl Chloride Reduction at Silver Cathodes

Published:2010-11-11 Issue:48 Volume:132 Page:17199-17210
ISSN:0002-7863
Container-title:Journal of the American Chemical Society
language:en
Short-container-title:J. Am. Chem. Soc.

Author:

Huang Yi-Fan¹,Wu De-Yin¹,Wang An¹,Ren Bin¹,Rondinini Sandra¹,Tian Zhong-Qun¹,Amatore Christian¹

Affiliation:

1. State Key Laboratory of Physical Chemistry of Solid Surfaces and College of Chemistry and Chemical Engineering, Xiamen University, 361005 Xiamen, China, Dipartimento di Chimica Fisica ed Elettrochimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milan, Italy, and Département de Chimie, Ecole Normale Supérieure, UMR 8640, 24 Rue Lhomond, F-75231 Paris Cedex 5, France

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Link

https://pubs.acs.org/doi/pdf/10.1021/ja106049c

Reference81 articles.

1. In the classical view the nonconcerted reductive cleavage of aromatic halides proceeds by electron injection into the low energy π* aryl orbital. This is then transferred into the σ* C−Cl one when its energy becomes reduced following its vibrational elongation. However, this does not account for the requirement of a significant overlap between the two molecular orbitals which remain orthogonal in such a process. Thus, an out-of-plane bending of the C−Cl bond in PhCl was shown recently to be crucial for allowing the cleavage of the C−Cl bond. See the following:

2. On the Dissociation of Aromatic Radical Anions in Solution. 1. Formulation and Application to p-Cyanochlorobenzene Radical Anion

3. On the Dissociation of Aromatic Radical Anions in Solution. 2. Reaction Path and Rate Constant Analysis

4. Electron transfer and bond breaking. Examples of passage from a sequential to a concerted mechanism in the electrochemical reductive cleavage of arylmethyl halides

5. Dissociative Electron Transfer to Haloacetonitriles. An Example of the Dependency of In-Cage Ion-Radical Interactions upon the Leaving Group

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