American Chemical Society
ol201620g_si_004.cif (13.56 kB)

Regio- and Stereoselective Synthesis of Multisubstituted Olefins and Conjugate Dienes by Using α-Oxo Ketene Dithioacetals as the Building Blocks

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posted on 2011-08-19, 00:00 authored by Weiwei Jin, Wangming Du, Qin Yang, Haifeng Yu, Jiping Chen, Zhengkun Yu
An efficient palladium(0)-catalyzed, Cu(I)-mediated synthetic route to trisubstituted olefins and conjugate dienes has been developed via oxo directing Liebeskind–Srogl cross-coupling reactions of gem-dihaloolefin-type α-oxo ketene dithioacetals with aryl and alkenylboronic acids. The synthetic protocol has demonstrated rare examples of transition-metal-promoted transformations of ketene dithioacetals, providing a novel route to highly functionalized conjugate dienes.