Premium
Modifiable Sulfur Tethers as Directing Groups for Aromatic CH Acetoxylation Reactions
Author(s) -
Richter Heinrich,
Beckendorf Stephan,
Mancheño Olga García
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000941
Subject(s) - chemistry , sulfoxide , reactivity (psychology) , sulfur , catalysis , redox , palladium , selectivity , combinatorial chemistry , dimethyl sulfoxide , aromaticity , organic chemistry , molecule , medicine , alternative medicine , pathology
Abstract A designed new class of modifiable sulfur tethers for aromatic CH bond functionalizations is presented. As a model, the palladium‐catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido‐redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S‐tether is also exemplified.