- Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds
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Site selectivity represents a key challenge for non-directed C-H functionalization, even when the C-H bond is intrinsically reactive. Here, we report a copper-catalyzed method for benzylic C-H azidation of diverse molecules. Experimental and density functional theory studies suggest the benzyl radical reacts with a CuII-azide species via a radical-polar crossover pathway. Comparison of this method with other C-H azidation methods highlights its unique site selectivity, and conversions of the benzyl azide products into amine, triazole, tetrazole, and pyrrole functional groups highlight the broad utility of this method for target molecule synthesis and medicinal chemistry.
- Suh, Sung-Eun,Chen, Si-Jie,Mandal, Mukunda,Guzei, Ilia A.,Cramer, Christopher J.,Stahl, Shannon S.
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supporting information
p. 11388 - 11393
(2020/07/21)
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- Gold(i) triazolyls: Organometallic synthesis in air and aqueous media
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(N-heterocyclic carbene)gold(i) alkynyls and organic azides have undergone cycloadditions in water-t-butanol mixtures with copper metal as the pre-catalyst to give new gold(i) triazolyls in high purity. Substrate tolerability was outlined for organoazides bearing a range of functional groups, and branching alpha to the azide moiety. All products are validated by combustion analysis or high-resolution mass spectrometry; two are also confirmed crystallographically.
- Heckler, James E.,Deligonul, Nihal,Rheingold, Arnold L.,Gray, Thomas G.
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supporting information
p. 5990 - 5992
(2013/07/25)
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- Substituted aminoalkyl biphenyl compounds and method of treating fungal infections
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Antimycotically-active compounds of the formula STR1 wherein R1 and R2 each independently are hydrogen, C1-7 -alkyl or C2-7 -alkenyl or together are a straight chain C2-4 -alkylene; R3 and R4 each independently are hydrogen or C1-7 -alkyl; R5 and R6 each independently are hydrogen, halogen, trifluoromethyl, nitro, cyano, C1-7 -alkoxy or C1-7 -alkyl; and Q is an unsubstituted or substituted phenyl or naphthyl group, wherein the substituents are at least one of halogen, trifluoromethyl, cyano, nitro, C1-7 -alkyl, C1-7 -alkoxy; C2-10 -alkenyl; or a substituted or unsubstituted C1-10 -alkyl group wherein said substituents are at least one hydroxy group; and pharmaceutically acceptable acid addition salts thereof.
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