Regio- and Stereoselective Synthesis of Thiazole-Containing Triarylethylenes by Hydroarylation of Alkynes

Thiazole-containing
π-conjugated moieties are important structural
units in the development of new electronic and photochromic materials.
We have developed a Pd-catalyzed syn-hydroarylation
reaction of diaryl alkynes with thiazoles that provides access to
thiazole-containing triarylethylenes. Pd­(II) complexes derived from
Pd(0) species and carboxylic acids facilitated C–H functionalization
of the unsubstituted thiazole with high C5 selectivity. The catalytic
system was also compatible with other azoles, such as oxazoles and
a pyrazole, allowing the stereoselective syntheses of various trisubstituted
olefins.

噻唑类含π共轭基团是开发新型电子和光致变色材料中的关键结构单元。本研究团队开发了一种以Pd催化的 diaryl alkynes 与噻唑的协同氢芳基化反应，该反应可制备噻唑类三芳基乙基烯。由Pd(0)物种和羧酸衍生而来的Pd(II)配合物，促进了未取代噻唑的C-H官能化，并实现了高C5选择性的转化。此外，该催化体系亦适用于其他杂唑类化合物，如恶唑和吡唑，从而实现了多种三取代烯烃的对映选择性合成。