78600-32-5Relevant articles and documents
Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
Liu, Zhijian,Larock, Richard C.
, p. 347 - 355 (2007)
An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps.
1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines
Cho, Seoyoung,Wang, Qiu
supporting information, (2020/02/28)
ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic addition, and coupling with electrophilic partners. This strategy leverages the advantageous reactivity of organozincate intermediates, enabling the installation of various functionalities such as amine, azide, oxygen, sulfur, halide, alkynyl, aryl, vinyl, and alkyl groups in a modular manner for the synthesis of diverse aniline skeletons.
13C NMR Study of ortho-, meta- and para-Substituted Phenylhiphenylamines: Substituent Effect Correlations
Grimley, Eugene,Collum, David H.,Alley, Earl G.,Layton, Bobby
, p. 296 - 302 (2007/10/02)
The 13C chemical shifts of 11 substituted triphenylamines have been determined and the assignment of these resonances made using intensities, 1H and 19F couplings and predictions from bond additivity relationships. 13C chemical shifts at carbons bearing the substituent and at carbons ortho to the substituent correlated reasonably well with the Q parameter.A multiple regression analysis of chemical shifts with the field and resonance parameters of Swain and Lupton and the Q parameter produced significantly better correlations than those obtained when Q was omitted for these positions. 13C chemical shift correlations for carbons meta and para to the substituent were not significantly better than when Q was omitted.Significant correlations were obtained between field and resonance parameters and 13C chemical shifts of C-o and C-p, and C-i, C-o, C-m and C-p of the non-substituent bearing phenyl rings in ortho- and para-substituted phenyldiphenylamines, respectively.
