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Molecules 2001, 6(11), 852-868; doi:10.3390/61100852
Article

Amine and Titanium (IV) Chloride, Boron (III) Chloride or Zirconium (IV) Chloride-Promoted Baylis-Hillman Reactions

* ,  and
Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China
* Author to whom correspondence should be addressed.
Received: 27 April 2001 / Revised: 11 October 2001 / Accepted: 18 October 2001 / Published: 31 October 2001
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Abstract

The Baylis-Hillman reactions of various aryl aldehydes with methyl vinyl ketone at temperatures below -20oC using Lewis acids such as titanium (IV) chloride, boron (III) chloride or zirconium (IV) chloride in the presence of a catalytic amount of selected amines used as a Lewis bases afford the chlorinated compounds 1 as the major product in very high yields. Acrylonitrile can also undergo the same reaction to give the corresponding chlorinated product in moderate yield. A plausible reaction mechanism is proposed. However, if the reaction was carried out at room temperature (ca. 20oC), then the Z-configuration of the elimination product 3, derived from 1, was formed as the major product.
Keywords: Titanium (IV) chloride; boron (III) chloride; zirconium (IV) chloride; Bayliss-Hillman reaction; halogenation; Lewis base; amine Titanium (IV) chloride; boron (III) chloride; zirconium (IV) chloride; Bayliss-Hillman reaction; halogenation; Lewis base; amine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Shi, M.; Jiang, J.-K.; Cui, S.-C. Amine and Titanium (IV) Chloride, Boron (III) Chloride or Zirconium (IV) Chloride-Promoted Baylis-Hillman Reactions. Molecules 2001, 6, 852-868.

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