A silver(i)-catalyzed tandem cyclization/cross-coupling reaction of enynones with iodonium ylides to construct carbon–carbon double bonds has been developed.
Pd(PPh3)2Cl2-catalyzed selective
tandem cyclization/oxidation of available conjugated diazo ene-yne-ketones
under O2 atmosphere led to the formation of diazo trisubstituted
furans. The Rh2(OAc)4-mediated selective C(sp2)–H insertion at the ortho-position
of 2-aryl group (R1) of the furan moiety under N2 atmosphere occurred to construct naphthalene cycle, affording trifunctionalized
naphtho[1,2-b]furans. C(sp2)–H
insertion at the 4-position of the furan ring, and Wolf rearrangement
of diazo moiety have not been observed.
We report the synthesis
of 4-(furan-2-yl)-3,4-dihydro-2H-pyrrol-2-one derivatives.
In this approach, two core structures,
the furan ring and 3,4-dihydro-2H-pyrrol-2-one, are
constructed via silver(I)-catalyzed cascade cyclization/cyclopropanation/ring-cleavage/nucleophilic
substitution reaction of enynones with enamines. A reasonable mechanism
has been proposed. This method possesses some advantages such as high
chemoselectivity, mild reaction conditions, simple operation, and
short reaction time.
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