ORGANIC
LETTERS
2006
Vol. 8, No. 1
19-22
A Convenient FeCl3-Catalyzed
Hydroarylation of Styrenes
Jette Kischel, Irina Jovel, Kristin Mertins, Alexander Zapf, and Matthias Beller*
Leibniz-Institut fu¨r Organische Katalyse an der UniVersita¨t Rostock e.V. (IfOK),
Albert-Einstein-Str. 29a, D-18059 Rostock, Germany
Received September 23, 2005
ABSTRACT
1,1-Diarylalkanes are easily synthesized by CH-functionalization reactions of electron-rich arenes and heteroarenes with styrenes in the presence
of FeCl3 as catalyst.
Arenes and heteroarenes are of outstanding importance for
the chemical industry as pharmaceuticals, agrochemicals, and
fine and bulk chemicals. Typically, well-known “classic”
transformations such as Friedel-Crafts alkylations, Friedel-
Crafts acylations, nitrations, and halogenations are used for
their functionalization. Although these methods work reliably
on large scale, they have significant drawbacks such as the
necessity of drastic reaction conditions (high temperature,
strong acidic conditions), regioselectivity problems, and large
amounts of (salt) byproducts. Often the incorporation of a
certain defined C-C-bond onto the aromatic core requires
several steps including introduction of activating groups or
protection and deprotection steps. Thus, the development of
direct C-C coupling reactions of arenes is an important and
ongoing task in organic synthesis.
alcohols,8 and the cyclization of arene-alkyne substrates9 are
elegant examples of this.
In this respect we demonstrated that various late transition
metal catalysts such as IrCl3, RhCl3, and H2PtCl6 catalyze
the addition of benzylic acetates, alcohols, and carbonates
to arenes and heteroarenes.10 Most of the reactions gave high
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4575.
Recently, organometallic chemistry and catalysis have
become efficient tools for the development of more envi-
ronmentally benign C-H transformations of arenes.1 The
addition of olefins to acetophenones (Murai reaction)2 and
aromatic imines,3 novel additions of olefins to arenes4,5 and
heterocycles,6 the addition of aromatics to alkynes7 or
(1) Dyker, G. Angew. Chem. 1999, 111, 1808-1822; Angew. Chem.,
Int. Ed 1999, 38, 1698-1712.
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Sonoda, M.; Chatani, N. Nature 1993, 366, 529-531. (b) Kakiuchi, F.;
Sekine, S.; Tanaka, Y.; Kamatami, A.; Sonoda, M.; Chatani, N.; Murai, S.
Bull. Chem. Soc. Jpn. 1995, 68, 62-83. (c) Kakiuchi, F.; Murai, S. Acc.
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Y.; Chatani, N.; Murai, S.; J. Mol. Catal. A: Chem. 2002, 182, 511-514.
(e) Guari, Y.; Castellanos, A.; Sabo-Etienne, S.; Chaudret, B. J. Mol. Catal.
A: Chem. 2004, 212, 77-82.
10.1021/ol0523143 CCC: $33.50
© 2006 American Chemical Society
Published on Web 12/06/2005