36321-73-0Relevant articles and documents
Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
Burgos, Carlos H.,Barder, Timothy E.,Huang, Xiaohua,Buchwald, Stephen L.
, p. 4321 - 4326 (2007/10/03)
(Chemical Equation Presented) A variety of diaryl ethers were synthesized by the Pd-catalyzed reaction of (hetero)-aryl halides and phenols. These reactions were achieved through the use of two new di-tert-butylphosphino biaryl ligands that overcome several limitations of previously described methods.
Use of tunable ligands allows for intermolecular Pd-catalyzed C-O bond formation
Vorogushin, Andrei V.,Huang, Xiaohua,Buchwald, Stephen L.
, p. 8146 - 8149 (2007/10/03)
Bulky biaryl phosphine ligands facilitate Pd-catalyzed C-O coupling reactions of aryl halides with primary and secondary alcohols by promoting reductive elimination at the expense of β-hydride elimination. The key to their success is the ability to match the size of the ligand to that of the combination of substrates. The efficient coupling of a number of unactivated aryl chlorides and bromides with cyclic and acyclic secondary alcohols was achieved. This included the coupling of allylic alcohols for the first time in a Pd-catalyzed coupling process.
Pd catalyzed coupling of 1,2-dibromoarenes and anilines: Formation of N,N-diaryl-o-phenylenediamines
Wenderski, Todd,Light, Kenneth M.,Ogrin, Doug,Bott, Simon G.,Harlan, C. Jeff
, p. 6851 - 6853 (2007/10/03)
1,2-Dibromoarenes were coupled with aniline derivatives to yield N,N-diaryl-o-phenylenediamines in moderate to good yield using a palladium/phosphine or palladium/carbene catalyst system. Under similar conditions, 1,2,4,5-tetrabromobenzene was coupled with aniline derivatives to produce the corresponding tetrasubstituted derivatives which are oxidized on workup to yield azophenines. The sequential reaction of two different anilines with 1-chloro-2-iodobenzene afforded mixed N,N-diaryl-o-phenylenediamines.
Synthesis of annulated dioxins as electron-rich donors for cation radical salts
Hellberg, Jonas,Dahlstedt, Emma,Pelcman, Margit E.
, p. 8899 - 8912 (2007/10/03)
The synthesis of a series of new alkoxylated linearly annulated dioxins is described together with their cyclic voltammetric behavior and some preliminary result on their ability to form cation radical salts. Of these dioxins, seven (8, 12, 19, 21, 27, 33, 34) are the first representatives of entirely new heterocyclic systems. Dioxins 8, 21, 22 and 27 gave good quality cation radical salts upon electrocrystallization. Graphical Abstract
Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
, p. 439 - 443 (2007/10/02)
The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.