Beilstein J. Org. Chem.2021,17, 2848–2893, doi:10.3762/bjoc.17.196
the carboamination of activated alkenes 115 with alkyldiacylperoxides 163 and acetonitrile (Scheme 34) [136]. Their efficient protocol featured a broad substrate scope, including diversely functionalized styrene derivatives, various alkyldiacylperoxides, and a few different nitrile solvents which
alcohols 67 and aliphatic acids 173 (Scheme 37) [144]. Through a DCC-mediated dehydrogenative condensation with hydroperoxides, carboxylic acids could generate alkyldiacylperoxides and peresters in situ. Decarboxylation followed by radical addition across the alkene 108 would generate a succeeding alkyl
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Graphical Abstract
Figure 1:
Price comparison among iron and other transition metals used in catalysis.
Beilstein J. Org. Chem.2018,14, 2916–2922, doi:10.3762/bjoc.14.270
from alkyldiacylperoxides, azidotrimethylsilane, and terminal alkynes is reported. The alkyl carboxylic acids is for the first time being used as the alkyl azide precursors in the form of alkyldiacylperoxides. This method avoids the necessity to handle organic azides, as they are generated in situ
, making this protocol operationally simple. The Cu(I) catalyst not only participates in the alkyldiacylperoxides decomposition to afford alkyl azides but also catalyzes the subsequent CuAAC reaction to produce the 1,2,3-triazoles.
Keywords: alkyldiacylperoxides; azidotrimethylsilane; click reaction
.
Furthermore, the scope of the alkyldiacylperoxides was then studied (Scheme 3). The alkyldiacylperoxides 2 were synthesized from the corresponding aliphatic carboxylic acids in a single step by DCC-mediated dehydrative condensation with hydrogen peroxide, and were used directly after simple filtration
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Graphical Abstract
Scheme 1:
General methods for the synthesis of triazoles.