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Synthesis 2009(3): 445-463  
DOI: 10.1055/s-0028-1083309
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Biaryls, Fluorenones, Cyclopenta[def]phenanthren-4-ones, and Benzophenones Based on Formal [3+3] Cyclocondensations of 1,3-Bis(silyloxy)buta-1,3-dienes with 3-(Silyloxy)-2-en-1-ones

Stefanie Reima, Matthias Laua, Muhammad Adeela, Ibrar Hussaina, Mirza A. Yawera, Abdolmajid Riahia, Zafar Ahmeda, Christine Fischerb, Helmut Reinkea, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 6 August 2008
Publication Date:
09 January 2009 (online)

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Abstract

Functionalized fluorenones were efficiently prepared in four steps. The [3+3] cyclization of 1,3-bis(silyloxy)buta-1,3-dienes with 3-(silyloxy)-2-en-1-ones afforded salicylates that were transformed into their enol triflates. The Suzuki cross-coupling reaction of the latter with arylboronic acids afforded 2-(methoxycarbonyl)biaryls that were subsequently transformed into the target molecules by intramolecular Friedel-Crafts acylation. In addition, 1-hydroxyfluorenones were prepared by cyclization of 3-aryl-3-(silyloxy­)-2-en-1-ones with 1,3-bis(silyloxy)buta-1,3-dienes and subsequent intramolecular Friedel-Crafts acylation of the 6-aryl­salicylates thus formed. In this context, the synthesis of novel cyclopenta[def]phenanthren-4-ones is reported. In addition, the synthesis of functionalized benzophenones is reported.

Key words

cyclizations - fluorenones - regioselectivity - silyl enol ethers

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CCDC 626089 and CCDC 698467 contain the crystallographic details of 7b and 7ab. These data are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033, or deposit@ccdc.cam.ac.uk.