ORGANIC
LETTERS
2006
Vol. 8, No. 17
3717-3719
Efficient Metal-Catalyzed Hydroarylation
of Styrenes
Magnus Rueping,* Boris J. Nachtsheim, and Thomas Scheidt
Degussa Endowed Professorship, Institute of Chemistry and Chemical Biology,
Johann-Wolfgang Goethe UniVersity Frankfurt am Main, Max-Von-Laue-Str. 7,
D-60438 Frankfurt, Germany
Received May 27, 2006
ABSTRACT
A highly efficient metal-catalyzed hydroarylation of various styrenes has been developed. This new bismuth-catalyzed C
−H functionalization
provides straightforward access to a series of valuable 1,1-diarylalkane products.
The functionalization of arenes and heteroarenes is of great
importance in the synthesis of pharmaceuticals, agro-, and
fine chemicals, and various procedures for their acylation
and alkylation have been reported. Traditionally, these
transformations are performed by Friedel-Crafts reactions
with acyl or alkyl halides in combination with at least
equimolar quantities of Lewis acids. Typically, drastic
reaction conditions are employed resulting in low selectivities
and overalkylation. Additionally, the need of electrophile
preformation, coproduction of hydrogen halides, and a large
amount of salt byproducts can be a significant drawback.
Therefore, in view of the demand for efficient, economic,
and environmentally friendly processes, the development of
direct catalytic carbon-carbon bond-forming reactions of
arenes with prior unmodified substrates is an important task.
Recently, promising transition-metal- and acid-catalyzed
C-H transformations of arenes and heteroarenes have been
reported.1 Examples include the addition of olefins to
acetophenones2 and aromatic imines3 or the inter- and
intramolecular arylation of alkynes, alkenes,4,5 benzyl, and
propagyl alcohols.6,7 In this context, we recently demon-
strated that Bi(OTf)3 is a highly reactive catalyst for the
addition of benzyl alcohol and its derivatives to arenes and
heteroarenes.9 The resulting products obtained from the latter
8
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10.1021/ol0612962 CCC: $33.50
© 2006 American Chemical Society
Published on Web 07/25/2006