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Synthesis 2004(18): 3060-3064  
DOI: 10.1055/s-2004-834900
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones Catalyzed by Yb(OTf)3 Under Solvent-Free Conditions

Limin Wang*a, Jia Shenga, He Tiana, Jianwei Hana, Zhaoyu Fana, Changtao Qianb
a Institute of Fine Chemicals, Lab for Advanced Materials, East China University of Science and Technology, 130 Meilong Lu, Shanghai 200237, P. R. China
Fax: +86(21)64252758; e-Mail: wanglimin@ecust.edu.cn; e-Mail: wcathy@china.com;
b Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
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Publication History

Received 12 July 2004
Publication Date:
02 November 2004 (online)

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Abstract

An array of aromatic aldehydes undergoes crossed aldol condensation with ketones in the presence of a catalytic amount of Yb(OTf)3 under solvent-free conditions to afford the corresponding α,α′-bis(substituted benzylidene)cycloalkanones in excellent yields without occurrence of any side reactions. This method is very general, simple and environmental friendly in contrast with the existing methods, which use many classical Lewis acids. Furthermore, the catalyst can be recovered conveniently and reused efficiently without the loss of activity.

Key words

α,α′-bis(substituted benzylidene)cycloalkanones - crossed aldol condensation - Yb(OTf)3 - solvent-free