Aryl radical-induced desulfonylative: Ipso -substitution of diaryliodonium salts: An efficient route to sterically hindered biarylamines
By using vicinal aryl sulfonamide substituted diaryliodonium salts, a cascade of desulfonylation/aryl migration was promoted by triethylamine in the synthesis of sterically hindered biarylamines, which operated via a radical-induced reaction pathway. The products were readily converted into a variety of important synthons. Furthermore, coupling reactions of N-methyl biarylamine and 1,6-dibromopyrene provided a potentially attractive molecule in OLEDs.
Chen, Huangguan,Han, Jianwei,Wang, Limin
p. 5697 - 5700
(2020/06/09)
Palladium-Catalyzed Carboamination of Allylic Alcohols Using a Trifluoroacetaldehyde-Derived Tether
The selective palladium-catalyzed carboamination of allylic alcohols is reported on the basis of the use of an easily introduced trifluoroacetaldehyde-derived tether. Aminoalkynylation reactions were realized using alkynyl bromides and commercially available phosphine ligands. For aminoarylations, a new biaryl phosphine ligand, "Fu-XPhos", was introduced to overcome a competitive Heck pathway. The carboamination products were obtained in high yields and diastereoselectivity. The tether could be easily removed to give value-added amino alcohol building blocks.
Muriel, Bastian,Orcel, Ugo,Waser, Jerome
supporting information
p. 3548 - 3551
(2017/07/17)
Synthesis of novel fused azecine ring systems through application of the tert-amino effect
Novel fused azecine ring systems were synthesized via the microwave-assisted thermal isomerization of terphenyl or biphenyl-pyridazine compounds possessing a vinyl and a tert-amino group, through application of a new extension of the tert-amino effect. Substrates for the ring closure were prepared from ortho-dihalobenzene or pyridazinone by consecutive Suzuki couplings with ortho-sec-amino- and formylphenylboronic acids, followed by Knoevenagel condensation of the aldehydes obtained.
Dunkel, Petra,Túrós, Gy?rgy,Bényei, Attila,Ludányi, Krisztina,Mátyus, Péter
experimental part
p. 2331 - 2339
(2010/06/12)
Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: Discovery of new effective chiral ligands
(Chemical Equation Presented) The hemilabile ligand Me-DuPHOS(O) 2 has proven to be a successful ligand for the copper-catalyzed addition of diethylzinc to N-phosphinoylimines. The corresponding α-chiral amines were obtained in high yields (80-98%) and enantiomeric ratios (19.0:1 to 99.0:1 er). Furthermore, this Cu?2 catalytic system has been shown to be effective in the addition of diethylzinc to nitroalkenes and in the reduction of β,β-disubstituted vinyl phenyl sulfones. This paper describes a general structure/selectivity study in which the three ligand subunits (chiral phospholane-linker-labile coordinating group (Z)) are systematically modified and tested in the copper-catalyzed addition of diethylzinc to the N-phosphinoylimine 1 derived from benzaldehyde. This study led to the discovery of a new class of effective chiral ligands that combine a chiral phospholane unit and an achiral phosphine oxide.
Bonnaventure, Isabelle,Charette, Andre B.
p. 6330 - 6340
(2008/12/22)
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