6637-11-2Relevant articles and documents
Switchable regioselection of C-H thiolation of indoles using different TMS counterions
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
supporting information, p. 11864 - 11867 (2019/10/11)
A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
Vilsmeier Formylation and Glyoxylation Reactions of Nucleophilic Aromatic Compounds Using Pyrophosphoryl Chloride
Downie, Ian M.,Earle, Martyn J.,Heaney, Harry,Shuhaibar, Khamis F.
, p. 4015 - 4034 (2007/10/02)
Reactions of N,N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates. Key words: pyrophosphoryl chloride, N,N-dimethylformamide, methoxyarene, heterocyle, formylation