A series of coupling products have been prepared by a ruthenium(II)‐catalyzed direct ortho‐C–H arylation of 2‐(aryl/heteroaryl)‐substituted quinazolines with (hetero)aryl bromides. Tri(hetero)aryl‐substituted alkenes were also prepared by olefinic C–H activation of 2‐(2‐arylvinyl)quinazoline derivatives. High conversions and selectivities were achieved by choosing the appropriate ruthenium(II) carboxylate catalyst system, solvent, and reaction temperature. The possibility of a C(sp3)–H functionalization by applying an arylation/reduction reaction sequence was also demonstrated.
The
one-pot synthesis of a broad variety of dihydrofuroquinolines,
dihydrothienoquinolines, and dihydrobenzoquinolines is reported. The
combination of the Rh(I)-catalyzed hydroarylation of vinylpyridines
with the Pd(0)/Pd(II)-catalyzed direct C–H arylation in a Multicomponent-Multicatalyst
Reaction (MC)2R could be used to develop an efficient and
step-economic protocol for the rapid construction of molecular complexity.
A high-yielding synthesis of π-extended heteroarenes through
an efficient three-step-one-pot procedure and a highly enantioselective
synthesis of 6-alkylsubstituted dihydrobenzoquinolines are shown.
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