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Synfacts 2017; 13(06): 0645
DOI: 10.1055/s-0036-1590436
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Silylium Ion Catalyzed C–H Arylation of Hydrocarbons

Contributor(s):
Benjamin List
,
Lucas Schreyer
Shao B. Bagdasarian AL. Popov S. Nelson HM. * University of California, Los Angeles, USA
Arylation of Hydrocarbons Enabled by Organosilicon Reagents and Weakly Coordinating Anions.

Science 2017;
355: 1403-1407
Further Information

Publication History

Publication Date:
16 May 2017 (online)

 
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Key words

arylation - hydrocarbons - phenyl cation - silylium ion

Significance

The Nelson group reports a silylium ion catalyzed arylation of C(sp2)–H and C(sp3)–H bonds. By employing 2–5 mol% of precatalyst A in the presence of a trialkylsilane initiator, various aliphatic and aromatic hydrocarbons were arylated with variously functionalized trimethylsilyl fluorobenzenes.


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Comment

Previously, catalytic reactions involving highly reactive phenyl cation equivalents were limited to intramolecular transformations. The ­authors describe the formation of a β-silicon-­stabilized phenyl cation (equivalent) II, which is proposed to subsequently undergo intermolecular insertion into the C–H bond of a hydrocarbon present in large excess. Desilylation of the resulting Wheland intermediate furnishes the product and regenerates the catalytically active species I.


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