ORGANIC
LETTERS
2012
Vol. 14, No. 21
5392–5395
Synthesis of Indenes via Brønsted Acid
Catalyzed Cyclization of Diaryl- and Alkyl
Aryl-1,3-dienes†
Dahan Eom, Sangjune Park, Youngchul Park, Taekyu Ryu, and Phil Ho Lee*
Department of Chemistry, Kangwon National University, Chuncheon 200-701,
Republic of Korea
Received August 15, 2012
ABSTRACT
Substituted indenes can be synthesized via the Brønsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. In this approach, treatment
of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene
derivatives in good to excellent yields under mild conditions.
Indenes are important building blocks in organic1 and
organometallic chemistry2 and are present in many biolog-
ically and pharmaceutically active compounds.3 Thus,
the development of synthetic methods for indenes has been
a significant objective in organic synthesis. To date, a
variety of synthetic methods for formation of an indene
ring have been reported. These include the reduction or
dehydration of an indanone,4 the cyclization of phenylvi-
nyl derivatives or phenyl-substituted allyl alcohols,5 the
ring expansion of suitably substituted cyclopropenes,6 or
the FriedelÀCrafts cyclization of tetraaryl substituted
1,3-butadienes using an excess of a Lewis acid (10 equiv).7
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† Dedicated to Prof. Young Keun Chung on the occasion of his 60th birthday.
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10.1021/ol302271w
Published on Web 10/24/2012
2012 American Chemical Society