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用于通过Baylis-Hillman加合物与芳基硼酸交叉偶联合成三取代烯烃的铑氟磷灰石催化剂。

Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids.

作者信息

Kantam M Lakshmi, Kumar K B Shiva, Sreedhar B

机构信息

Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India.

出版信息

J Org Chem. 2008 Jan 4;73(1):320-2. doi: 10.1021/jo701982m. Epub 2007 Dec 12.

DOI:10.1021/jo701982m
PMID:18072787
Abstract

Treatment of fluorapatite (prepared by incorporating basic species F(-) in apatite in situ by coprecipitation) with an aqueous solution of RhCl(3) resulted in rhodium-exchanged fluorapatite catalyst (RhFAP), which successfully promoted cross coupling of Baylis-Hillman adducts with arylboronic acids to yield trisubstituted olefins. A variety of arylboronic acids and Baylis-Hillman adducts were converted to the corresponding trisubstituted olefins, demonstrating the versatility of the reaction. The reaction is highly stereoselective. RhFAP was recovered quantitatively by simple filtration and reused with almost consistent activity.

摘要

用RhCl(3)水溶液处理氟磷灰石(通过共沉淀法原位将碱性物种F(-)掺入磷灰石中制备),得到铑交换的氟磷灰石催化剂(RhFAP),该催化剂成功地促进了Baylis-Hillman加合物与芳基硼酸的交叉偶联反应,生成三取代烯烃。多种芳基硼酸和Baylis-Hillman加合物都能转化为相应的三取代烯烃,证明了该反应的通用性。该反应具有高度的立体选择性。通过简单过滤可定量回收RhFAP,并能以几乎一致的活性重复使用。

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