A class of 2-aminopyridine
1-oxides are discovered to be effective
ligands for the Cu-catalyzed amination of less reactive (hetero)aryl
chlorides. A wide range of functionalized (hetero)aryl chlorides reacted
with various aliphatic amines to afford the desired products in good
to excellent yields under the catalyst of CuI/2-aminopyridine 1-oxides.
Furthermore, the catalyst system worked well for the coupling of cyclic
secondary amines and N-methyl benzylamine with (hetero)aryl
chlorides.
The
construction of a seven-membered ring in the polycyclic aromatic
hydrocarbon skeleton remains a notoriously difficult but attractive
challenge. Herein a novel palladium-catalyzed [4 + 3] decarboxylative
annulation of 2-iodobiphenyls with 2-(2-halophenyl)acrylic acids is
reported, which provides an efficient approach for assembling various
tribenzo[7]annulenes via a C–H activation and decarboxylation
process. Moreover, tribenzo[7]annulenes can be also synthesized via
a [2 + 2 + 3] decarboxylative annulation strategy by employing readily
available 1,2-halobenzenes, phenylboronic acids, and 2-(2-halophenyl)acrylic
acids.
Until now, cascade reactions involving five-membered C,C-palladacycles rely heavily on Pd(0)-catalyzed
C–H functionalization of aryl halides initiated by carbopalladation.
Herein, we report a novel Pd(II)-catalyzed cascade decarboxylative
cyclization of o-alkynylanilines initiated by aminopalladation.
In this protocol, o-alkynylanilines undergo sequential anti aminopalladation, C–H activation, and dealkylation
to form C,C-palladacycles, which
are then trapped by o-bromobenzoic acids or 8-bromo-1-naphthoic
acid to produce diverse polycyclic heteroarenes, such as dibenzo[a,c]carbazoles and multiple arene-fused
cyclohepta[1,2-b]indoles.
Herein a novel palladium-catalyzed tandem decarboxylative biscyclization of o-alkynylanilines with o-chlorobenzoic acids has been reported, which provides an efficient approach for the assembly of dibenzo[a,c]carbazoles. This protocol employs an intramolecular...
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