In this study, the first highly chemoselective amidation of Boc and amide groups of N -R- N -Boc arylamides is advanced. This practical and operationally-simple method enables the preparation of either N -aroylureas or imides in good to excellent yields without addition of transition metals. The choice of base plays a significant role in controlling the reactivity of the inequivalent carbonyl groups. The amidation of the Boc group was observed with arylamides, ArCONH 2 , when subjected to KO t Bu while imides were produced with LiOH. DFT studies are employed to explore the divergent mechanisms. It is anticipated that these chemoselective methods will be of interest to the synthetic and medicinal chemistry communities.
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Triarylmethanols are well-known core structures in natural products and pharmacologically relevant compounds. In general, transition metal-based catalysts or highly reactive organometallics are employed for the synthesis of these compounds. Herein, we report the regioselective tandem C(sp 3 )–H arylation/oxidation of diarylmethanes with nitroarenes to generate arylated alcohols. The present method is general, mild, green, and conducted in air at room temperature. Furthermore, use of triarylmethanes as pro-nucleophiles provides straightforward access to select tetraarylmethanes through a cross-dehydrogenative coupling process.more » « less
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The imide moiety is a well-known structural motif in bioactive compounds and a useful building block in a variety of processes. Using N -acylglutarimides with MN(SiMe 3 ) 2 and either N -acylpyrroles or aryl esters, an operationally convenient method to produce a wide array of diaryl- and alkyl arylimides is presented. Symmetric imides are also accessible when N -acylglutarimides are employed as acylation reagents under similar reaction conditions. A unique feature of this method stems from the use of two different electrophilic acylating reagents leading to the formation of the unsymmetrical imides with excellent chemoselectivity.more » « less
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Abstract A base‐promoted net‐[3+2] cycloaddition of nitriles and 1‐arylpropynes for the synthesis of pyrroles is described. The developed method provides convenient access to various 2,5‐disubstituted or 2,4,5‐trisubstituted pyrroles in 40% to 96% yields (32 examples). Among methods for the synthesis of pyrroles, the protocol presented here stands out for its convenience and atom‐economy.
