A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as...
The development of methods for the
assembly of 1,2,3-triazoles
is an important topic due to the broad applications of this motif
in various scientific fields. In this work, we demonstrate that the
three-component assembly of α-CF3 carbonyls, NaN3, and amines was achieved for the selective construction of
a variety of 5-amino NH-1,2,3-triazoles under transition-metal-free
and open-air conditions. The method provides a general and operationally
simple route to functionalized biologically important molecules including
carbohydrates, nucleosides, and peptides and exhibits broad substrate
scopes. We further demonstrate that the NH-1,2,3-triazoles
can be smoothly converted to the regiospecific N-2
alkylated 1,2,3-triazole products. Mechanistic studies based on experiments
and density functional theory calculations showed that this transformation
proceeds via defluorination-initiated programmed substitution/cyclization/H-transfer
to give the 4,5-difunctionalized captodative NH-1,2,3-triazole
product.
The
concurrent incorporation of a germyl fragment and another functional
group (beyond the hydrogen atom) across the CC double bond
is a highly appealing yet challenging task. Herein we demonstrate
the efficient germyl peroxidation of alkenes with germanium hydrides
and tert-butyl hydroperoxide via a copper-catalyzed
three-component radical relay strategy. This protocol exhibits excellent
functional group tolerance and exquisite chemo- and regioselectivity
under mild conditions and represents a rare example of constructing
synthetically challenging metal-embedded organic peroxides.
The incorporation of a germyl group and another functional
fragment
across the CC bond is a challenging task due to the prevailing
hydrogermylation reaction. Herein, an efficient copper-catalyzed three-component
reaction of alkenes, germanium hydrides, and trimethylsilyl azide
has been disclosed. This transformation allows the concomitant introduction
of germyl and azide groups across the double bonds in a highly regioselective
manner with tert-butyl hydroperoxides as the bystanding
oxidant. The resulting β-germyl azides could be easily converted
into β-germyl amine and 1,2,3-triazoles of significant value.
The light-promoted regioselective germylation of aryl propiolamides/alkynoates with germanium hydrides is reported. The germyl-containing spiro[4.5]trienones were obtained when N-arylpropiolamides were used via sequential CÀ Ge and CÀ C bond formation, while aryl alkynoates delivered the vinylgermanes with radical Smiles rearrangement and CO 2 release.
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