4.7 Article

Sequential Pd(0)/Fe(III) Catalyzed Azide-Isocyanide Coupling/Cyclization Reaction: One-Pot Synthesis of Aminotetrazoles

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 16, 页码 9530-9537

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01261

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  1. Central University of Rajasthan
  2. DST [EMR/2016/003969, EMR/2016/008016]
  3. CSIR [02(0201)/14/EMR-II]

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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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