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Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds.

08:00 EDT 8th April 2019 | BioPortfolio

Summary of "Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds."

Ethynylbenziodoxol(on)es (EBXs) cyclic hypervalent iodine reagents are now established reagents for the alkynylation of radicals and nucleophiles, yet they present limited possibilities for further structure and reactivity modification. Herein, we report the first synthesis of the corresponding Ethynylbenziodazolones (EBZs) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen. The substituent on the nitrogen enables further fine-tuning of the reagent structure and reactivity. EBZ reagents were easily obtained from the corresponding benzamides using a one-step procedure, and displayed a reactivity comparable to that of EBX reagents. In particular, they were applied in an asymmetric copper-catalyzed oxyalkynylation of diazo compounds, which proceeded in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.

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Name: Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
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