Journal of Organic Chemistry p. 9530 - 9537 (2018)
Update date:2022-08-05
Topics:
Pathare, Ramdas S.
Ansari, Arshad J.
Verma, Sarika
Maurya, Anand
Maurya, Antim K.
Agnihotri, Vijai K.
Sharon, Ashoke
Pardasani, Ram T.
Sawant, Devesh M.
A rapid and efficient synthesis of aminotetrazole from aryl azides, isocyanides, and TMSN3 is developed. The reaction is promoted by sequential Pd(0)/Fe(III) catalysis. The reaction sequence utilizes the Pd-catalyzed azide-isocyanide denitrogenative coupling reaction to generate unsymmetric carbodiimide in situ, which reacts with TMSN3 in the presence of FeCl3 in a single pot. The methodology has distinct advantages over traditional synthetic approaches where toxic Hg and Pb salts are employed at stoichiometric scale.
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