Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation

被引：26
作者：
Barrett, Matthew J. [1 ]
Davies, Paul W. [1 ]
Grainger, Richard S. [1 ]
机构：
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 32期
基金：
英国工程与自然科学研究理事会;
关键词：
C-H ACTIVATION; SULFUR MONOXIDE TRANSFER; OXYGEN-ATOM TRANSFER; QUINOLINE N-OXIDES; EFFICIENT SYNTHESIS; GOLD(I)-CATALYZED REARRANGEMENT; OXIDATIVE CYCLOPROPANATION; BIOLOGICAL-ACTIVITY; MASKED YLIDES; DERIVATIVES;
D O I：
10.1039/c5ob01241d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A protocol has been developed for direct Csp(3)-Csp(2) bond formation at the 4- and 6-positions of dibenzothiophenes using a gold(I) catalyst with terminal alkynes and dibenzothiophene-S-oxides. The sulfoxide acts as a traceless directing group to avoid the need to prefunctionalise at carbon. The iterative use of this protocol is possible and has been employed in the preparation of novel macrocyclic structures. In addition, a cascade process shows how oxyarylations can be combined with other processes resulting in complex, highly efficient transformations.
引用
收藏
页码：8676 / 8686
页数：11
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