A fluorescence-based assay for high-throughput screening of coupling reactions. Application to Heck chemistry

被引:303
|
作者
Shaughnessy, KH [1 ]
Kim, P [1 ]
Hartwig, JF [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1021/ja983419m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new fluorescence-based assay for high-throughput screening of reactions that couple two organic molecules is described. The assay involves reaction of one substrate containing a tethered fluorophore with a second molecule that is attached to a solid support. A successful coupling process is signaled by fluorescence of the solid support, which can be isolated by either simple centrifugation or filtration. To evaluate this assay in the context of a catalytic process under intense current study, we searched for improved, readily available phosphines for Heck chemistry. An acrylate containing a tethered coumarin was reacted with an aryl halide supported on a cross-linked polystyrene resin. Comparison of the results from our fluorescence-based assay with results from serial GC analysis showed that the fluorescence-based assay accurately selected the most active ligands for the Heck coupling of aryl bromides and chlorides. Two ligands chosen by the assay, tri (tert-butyl)phosphine and di(tert-butylphosphino)ferrocene, were found to be the most active systems to date for the olefination of unactivated aryl bromides, and di(tert-butylphosphino)ferrocene is the most efficient ligand for olefination of unactivated aryl chlorides.
引用
收藏
页码:2123 / 2132
页数:10
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