The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp C-H bonds of anilides in the presence of catalytic Pd(OAc) and KSO as an oxidant in MsOH/CFCOH (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.
A novel naphthalimide molecule, 4-(2-methoxyethoxy)-N-butyl-1,8-naphthalimide (MEBN), has been synthesized and characterized. The UV-visible absorption and fluorescence emission spectral properties in n-hexane, toluene, CHCl 3 , and CH 3 OH were studied. Its optical properties depend on solvent polarity. The application of MEBN in cell imaging was investigated.
The unsymmetrical biaryls (Ar1–Ar2) produced by the catalytic cross-couplings
of aryl halides (Ar1–halo) with aryl metallics (Ar2–M)
in the loading ratio of 1:1 are popular in chemical synthesis. In
contrast, there has been less precedence on the same biaryls produced
effectively from two normal aryl C–H bonds with equivalent
loading. Here, we report that, in a palladium/oxidant/acid catalytic
system at room temperature, one arene (Ar1–H, 1
equiv) can highly selectively couple with the other one (Ar2–H, 1 equiv) to afford the target Ar1–Ar2 just by controlling the directing groups and the substituted
groups on their phenyl rings. The utility of this one–one cross-coupling
is also demonstrated by synthesis of a few bioactive molecules.
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