A visible-light-induced highly selective alkylation and amination of unactivated C(sp 3 )-H bonds via the synergistic effects of an organo-photoredox catalyst and a bromine-based hydrogen atom transfer agent has been developed by applying CH 2 Br 2 as both the solvent and the bromine radical source. Our study offers a new paradigm for the direct synthesis of valuable compounds from abundant alkane feedstocks in a convenient and metal-free manner.
A highly stereoselective sequential annulation reaction between γ-substituted allenoates and ketimines was reported. By using bifunctional N-acyl aminophosphine catalysts, poly-heterocycle rings were obtained with high stereocontrol in good to excellent yields. The desired products have four contiguous stereogenic centers (one quaternary and three tertiary carbon centers), and only one isomer was obtained in all reactions.
Divergent
domino annulation reactions of sulfur ylides and azadienes
were developed. A wide range of functionalized benzofuran-fused six-
and seven-membered nitrogen–heterocyclic compounds were prepared
in moderate to excellent yields under mild conditions. It is worth
noting that the crotonate-derived sulfur ylides could be used as a
novel C2 synthon or C3 synthon selectively by simply transforming
the base.
A convenient and efficient Cu(OAc)2-mediated N-heteroannulation reaction of [60]fullerene with N-sulfonylated o-amino-aromatic methyl ketones or O-alkyl oximes has been reported for the synthesis of novel and scarce [60]fullerene-fused tetrahydroazepinones and -azepinonimines in a highly selective manner. Moreover, a possible mechanism involving two pathways is proposed on the basis of the experimental observations.
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