Fleming-Tamao oxidation
Encyclopedia
The Fleming–Tamao oxidation is the organic oxidation of alkyl silanes into alcohol
s with peroxide
s. The research groups of Fleming and Tamao developed procedures for this reaction in parallel to one another. It is especially useful since it allows alcohols to be masked as much more resilient silanes through a synthesis, before stereospecific removal. The reactions are often grouped together since they are mechanistically similar and perform the same transformation, there is no clear choice between them and it is often decided by trying both. An example of this is shown in a synthesise of two different carbasugars each synthesis using one of the methods.
The Fleming reaction has recently been reviewed
A recent development has extended this methodology to aromatic systems, allowing substituted phenols to be readily synthesised via aryl silane oxidation. One notable feature of this reaction is the use of catalytic amounts of a fluoride source to achieve the desired oxidation.
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
s with peroxide
Peroxide
A peroxide is a compound containing an oxygen–oxygen single bond or the peroxide anion .The O−O group is called the peroxide group or peroxo group. In contrast to oxide ions, the oxygen atoms in the peroxide ion have an oxidation state of −1.The simplest stable peroxide is hydrogen peroxide...
s. The research groups of Fleming and Tamao developed procedures for this reaction in parallel to one another. It is especially useful since it allows alcohols to be masked as much more resilient silanes through a synthesis, before stereospecific removal. The reactions are often grouped together since they are mechanistically similar and perform the same transformation, there is no clear choice between them and it is often decided by trying both. An example of this is shown in a synthesise of two different carbasugars each synthesis using one of the methods.
The Fleming reaction has recently been reviewed
A recent development has extended this methodology to aromatic systems, allowing substituted phenols to be readily synthesised via aryl silane oxidation. One notable feature of this reaction is the use of catalytic amounts of a fluoride source to achieve the desired oxidation.