63254-50-2Relevant articles and documents
Ethynylbenziodazolones (EBZ) as Electrophilic Alkynylation Reagents for the Highly Enantioselective Copper-Catalyzed Oxyalkynylation of Diazo Compounds
Hari, Durga Prasad,Schouwey, Lionel,Barber, Verity,Scopelliti, Rosario,Fadaei-Tirani, Farzaneh,Waser, Jerome
supporting information, (2019/05/28)
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.
Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds
Hari, Durga Prasad,Waser, Jerome
supporting information, p. 8420 - 8423 (2017/07/06)
Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds usi
N,N′-ditosylhydrazine: A convenient reagent for facile synthesis of diazoacetates
Torna, Tatsuya,Shimokawa, Jun,Fukuyama, Tohru
, p. 3195 - 3197 (2008/02/10)
A novel entry to the synthesis of diazoacetates is disclosed. A variety of diazoacetates were synthesized from the corresponding bromoacetates by treatment with N,N′-ditosylhydrazine in moderate to high yields. Ease of operation with the stable crystalline reagent as well as a short reaction time offer a useful alternative to the conventional methods.