Chelation-assisted β-selective direct C-H bond arylation of 2-thienylthioamide catalyzed by Pd-1,10-phenanthroline complexes

Chelation-assisted β-selective direct C-H bond arylation of 2-thienylthioamide catalyzed by Pd-1,10-phenanthroline complexes
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Pd-1,10-菲咯啉配合物催化的2-噻吩基硫代酰胺的螯合辅助β-选择性直接C-H键芳基化

DOI:
10.1002/ajoc.201800160
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发表时间:
2018
影响因子:
2.7
通讯作者:
Murai Toshiaki
Murai Toshiaki
中科院分区:
化学3区
文献类型:
--
作者:
Shibahara Fumitoshi;Asai Yusuke;Murai Toshiaki

文献摘要

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研究了钯-1,10-邻菲咯啉催化的噻吩硫代酰胺的螯合辅助β-选择性直接C-H键芳基化反应。所用的碱对反应性有重要影响:用K2 CO 3进行β-选择性(3-选择性)反应,使用Cs2 CO 3将α-和β-位芳基化,得到3,5-二芳基化产物。通过噻吩基硫代酰胺和催化剂前体的化学计量反应证实了螯合辅助的钯化,得到钯环。
A palladium–1,10‐phenanthroline‐catalyzed chelation‐assisted β‐selective direct C−H bond arylation of thienylthioamide was developed. The base used critically affected the reactivity: a β‐selective (3‐selective) reaction took place with K2CO3, and both the α‐ and β‐positions were arylated to give 3,5‐diarylated product with the use of Cs2CO3. The chelation‐assisted palladation affording palladacycles was confirmed by stoichiometric reactions of thienylthioamide and the catalyst precursor.