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 Reim; Matthias Lau; Muhammad Adeel; Ibrar Hussain; Mirza A. Yawer; Abdolmajid Riahi; Zafar Ahmed; Christine Fischer; Helmut Reinke; Peter Langer

doi:10.1055/s-0028-1083309

PAPER

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 Reim^a, Matthias Lau^a, Muhammad Adeel^a, Ibrar Hussain^a, Mirza A. Yawer^a, Abdolmajid Riahi^a, Zafar Ahmed^a, Christine Fischer^b, Helmut Reinke^a, 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

Abstract

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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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Referenzen

References

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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.