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Phenyl cation: A versatile intermediate
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DOI：10.1016/j.jphotochem.2017.02.007.png)
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Abstract
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Phenyl cations are short-lived electrophiles and can be smoothly generated by photolysis of aromatic halides (chlorides, fluorides) and esters (sulfonates, sulfates and phosphates) in protic media. Indeed, the heterolytic cleavage of an Aryl-LG bond (LG = leaving group; X, OR) allows for the generation of a triplet aryl cation (Ar-3(+)) that chemoselectively reacts with pi-bond nucleophiles to perform transition metal free arylations. Aryl cations can be also exploited in the generation of other high energy intermediates, such as diradicals (including ortho-arynes and alpha,n-didehydrotoluenes), potentially useful for medicinal applications. Since the generation of phenyl cations is always accompanied by the release of a strong acid (e.g. sulfonic acids), the phenyl cation precursors are actually non ionic photoacid generators (PAGs) that find useful applications in nanolithography. (C) 2017 Elsevier B.V. All rights reserved.
Keywords:
Phenyl cations
Diradicals
Metal-free arylations
Photoheterolysis
Photoacid generators (PAGs)
Journal
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4.7
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1.2W
Citations:
2.5W
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