Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids
Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids
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DOI：
10.1021/jo701982m
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发表时间：
2008-01-04
影响因子：
3.6
通讯作者：
Sreedhar, B.
中科院分区：
文献类型：
--
作者：
Kantam, M. Lakshmi;Kumar, K. B. Shiva;Sreedhar, B.
[图示]对于R-2=CN，得到了Z-异构体(99%)。氟磷灰石(通过共沉淀法在磷灰石中原位引入碱性物种F-制备)与RhCl3水溶液处理得到了Rh-交换型氟磷灰石催化剂(RhFAP)，它成功地促进了Baylis-Hillman加合物与芳基硼酸的交叉偶联，生成了三取代烯烃。各种芳基硼酸和Baylis-Hillman加合物被转化为相应的三取代烯烃，显示了反应的多功能性。该反应具有高度的立体选择性。通过简单的过滤，可定量回收RhFAP，并可重复使用，活性几乎一致。
[GRAPHICS]For R-2 = CN, Z-isomer (99%) was obtained.Treatment of fluorapatite (prepared by incorporating basic species F- in apatite in situ by coprecipitation) with an aqueous solution of RhCl3 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.