1484-39-5Relevant articles and documents
RUTHENIUM-CATALYSED REARRANGENMENTS OF AZOBENZENES II. THE PREPARATION OF 1-PHENYLBENZINIDAZOLES FROM AZOBENZENE DERIVATIVES AND PRIMARY ALCOHOLS CATALYSED BY RUTHENIUM COMPLEXES
Spencer, Alwyn
, p. 79 - 90 (1985)
RuCl3*3H2O in presence of PPh3 and a catalytic amount of a base and under an atmosphere of carbon monoxide catalyses the reaction of azobenzene derivatives and primary alcohols or their esters to give 2-substituted 1-phenylimidazoles.Substituents in the azobenzene derivatives have a marked effect on the product yields.Where isomer formation can occur, all possible isomers of the product are usually formed.In non-symmetrically substituted azobenzene derivatives, ortho-metallation occurs preferentially in the aromatic ring having the highest electron density.
Divergent strategy for the chemoselective synthesis of N-Arylbenzimidazoles and N-Arylindazoles from arylamino oximes
Li, Zhen-Hua,Sun, Xiao-Meng,Qin, Jin-Jing,Tan, Zhi-Yong,Wang, Wen-Biao,Ma, Yao
, (2020/01/28)
An efficient and divergent synthesis of N-arylbenzimidazoles and N-arylindazoles from arylamino oximes based on reaction conditions selection was developed. The synthesis was approached by treating oximes with BTC and the chemoselectivity was regulated by the amount of Et3N. This switchable N–N and N–C bond formation process features mild reaction conditions, simple execution, high chemoselectivity and broad substrate scope.
Efficient N-arylation of azole compounds utilizing selective aryl-transfer TMP-iodonium(III) reagents
Koseki, Daichi,Aoto, Erika,Shoji, Toshitaka,Watanabe, Kazuma,In, Yasuko,Kita, Yasuyuki,Dohi, Toshifumi
, p. 1281 - 1286 (2019/04/10)
It was determined that diaryliodonium(III) triflates bearing a trimethoxybenzene (TMP) auxiliary are more reactive than the reported selective aryl-transfer iodonium salts in the N-arylation of benzimidazoles and other types of azole compounds under catalytic conditions. The TMP-iodonium(III) salts can thus effectively facilitate the reaction at 50 °C or below, producing the corresponding N-arylated biaryls without the formation of TMP-derived coupling byproducts. Utilization of this TMP reagent under mild conditions would prevent the underlying problem of participation of the auxiliary group in the coupling reactions, which is observed while using the iodonium(III) salts that require elevated temperatures.
