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Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper‐Catalyzed Oxyalkynylation of Diazo Compounds
Author(s) -
Hari Durga Prasad,
Schouwey Lionel,
Barber Verity,
Scopelliti Rosario,
FadaeiTirani Farzaneh,
Waser Jerome
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900950
Subject(s) - diazo , hypervalent molecule , chemistry , reagent , reactivity (psychology) , electrophile , enantioselective synthesis , nucleophile , combinatorial chemistry , alkyne , catalysis , organic chemistry , substituent , medicine , alternative medicine , pathology
Ethynylbenziodoxol(on)e (EBX) 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, the first synthesis is reported for the corresponding ethynylbenziodazolone (EBZ) reagents, in which the oxygen atom in the iodoheterocycle is replaced by a nitrogen atom. The substituent on the nitrogen enables further fine‐tuning of the reagent structure and reactivity. EBZ reagents are obtained easily from the corresponding benzamides by using a one‐step procedure, and display reactivity comparable to that of EBX reagents. In particular, they are applied in an asymmetric copper‐catalyzed oxyalkynylation of diazo compounds, which proceeds in high yield and enantioselectivity for a broad range of substituents on the diazo compounds and the alkyne.