27484-67-9Relevant academic research and scientific papers
Rhodium-catalyzed synthesis of unsymmetric di(heteroaryl) compounds via heteroaryl exchange reactions
Arisawa, Mieko
, p. 643 - 648 (2019/04/30)
Unsymmetric di(heteroaryl) HetAr–X–HetAr′ compounds have flexible and rigid groups, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Then, synthesis of such compounds is critical for the development of drugs. Unsymmetric HetAr-X-HetAr′ compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. This method allows synthesis of unsymmetric HetAr–O–HetAr′, HetAr–S–HetAr′, and HetAr–CH2–HetAr′ compounds as well as HetAr–F compounds from heteroaryl aryl ethers and heteroaryl reagents. The rhodium-catalyzed heteroaryl exchange reaction was also applied to the synthesis of C–N-linked di(heteroaryl) compounds from N-benzoyl heteroarenes and heteroaryl aryl ethers. The synthesis has a broad applicability, which gives a diversity of novel unsymmetric HetAr–X–HetAr′ and C–N-linked di(heteroaryl)s compounds containing five- and six-membered heteroarenes.
Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides
Arisawa, Mieko,Tanii, Saori,Tazawa, Takeru,Yamaguchi, Masahiko
supporting information, p. 11390 - 11393 (2016/09/23)
A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.
