Novel Electrocatalytic Procedure for the Oxidation of Alcohols, Aldehydes, Cyclic Ketones, and C-H Bonds Adjacent to Olefinic or Aromatic Groups

Mark S. Thompson; Wagner F.De Giovani; Bruce A. Moyer; Thomas J. Meyer

doi:10.1021/jo00199a043

Novel Electrocatalytic Procedure for the Oxidation of Alcohols, Aldehydes, Cyclic Ketones, and C-H Bonds Adjacent to Olefinic or Aromatic Groups

Mark S. Thompson, Wagner F.De Giovani, Bruce A. Moyer, Thomas J. Meyer

Research output: Contribution to journal › Article › peer-review

111 Scopus citations

Abstract

A novel electrocatalytic procedure is described for the oxidation of primary and secondary alcohols, cyclic ketones, and C-H bonds adjacent to aromatic or olefinic groups. The procedure involves the use of the Ru^IV oxidant [Ru(trpy)(bpy)(O)]²⁺ (trpy is 2,2^',2^''-terpyridine; bpy is 2,2^'-bipyridine) in water at pH 6.8 or in dimethyl sulfone-water mixtures and is based on an electrochemical “shuttle” mechanism in which the Ru^IV complex is regenerated by electrochemical oxidation of [Ru^II(trpy)(bpy)(H₂o)]²⁺.

Original language	English
Pages (from-to)	4972-4977
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	49
Issue number	25
DOIs	https://doi.org/10.1021/jo00199a043
State	Published - Feb 1984
Externally published	Yes

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title = "Novel Electrocatalytic Procedure for the Oxidation of Alcohols, Aldehydes, Cyclic Ketones, and C-H Bonds Adjacent to Olefinic or Aromatic Groups",

abstract = "A novel electrocatalytic procedure is described for the oxidation of primary and secondary alcohols, cyclic ketones, and C-H bonds adjacent to aromatic or olefinic groups. The procedure involves the use of the RuIV oxidant [Ru(trpy)(bpy)(O)]2+ (trpy is 2,2',2''-terpyridine; bpy is 2,2'-bipyridine) in water at pH 6.8 or in dimethyl sulfone-water mixtures and is based on an electrochemical “shuttle” mechanism in which the RuIV complex is regenerated by electrochemical oxidation of [RuII(trpy)(bpy)(H2o)]2+.",

author = "Thompson, {Mark S.} and Giovani, {Wagner F.De} and Moyer, {Bruce A.} and Meyer, {Thomas J.}",

year = "1984",

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pages = "4972--4977",

journal = "Journal of Organic Chemistry",

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T1 - Novel Electrocatalytic Procedure for the Oxidation of Alcohols, Aldehydes, Cyclic Ketones, and C-H Bonds Adjacent to Olefinic or Aromatic Groups

AU - Thompson, Mark S.

AU - Giovani, Wagner F.De

AU - Moyer, Bruce A.

AU - Meyer, Thomas J.

PY - 1984/2

Y1 - 1984/2

N2 - A novel electrocatalytic procedure is described for the oxidation of primary and secondary alcohols, cyclic ketones, and C-H bonds adjacent to aromatic or olefinic groups. The procedure involves the use of the RuIV oxidant [Ru(trpy)(bpy)(O)]2+ (trpy is 2,2',2''-terpyridine; bpy is 2,2'-bipyridine) in water at pH 6.8 or in dimethyl sulfone-water mixtures and is based on an electrochemical “shuttle” mechanism in which the RuIV complex is regenerated by electrochemical oxidation of [RuII(trpy)(bpy)(H2o)]2+.

AB - A novel electrocatalytic procedure is described for the oxidation of primary and secondary alcohols, cyclic ketones, and C-H bonds adjacent to aromatic or olefinic groups. The procedure involves the use of the RuIV oxidant [Ru(trpy)(bpy)(O)]2+ (trpy is 2,2',2''-terpyridine; bpy is 2,2'-bipyridine) in water at pH 6.8 or in dimethyl sulfone-water mixtures and is based on an electrochemical “shuttle” mechanism in which the RuIV complex is regenerated by electrochemical oxidation of [RuII(trpy)(bpy)(H2o)]2+.

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JF - Journal of Organic Chemistry

IS - 25

ER -

Novel Electrocatalytic Procedure for the Oxidation of Alcohols, Aldehydes, Cyclic Ketones, and C-H Bonds Adjacent to Olefinic or Aromatic Groups

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