Visible Light Mediated Co-Catalyzed Isocyanide Insertion with Sulfonyl Azide: Synthesis of Sulfonyl Carbamimidic Azide and Sulfonyl Aminotetrazole via Carbodiimide Intermediate

Sundaresan Ravindra; Kannan Natarajan; Vetrivel R Padma Priya; Ramesh Kataria; Ganesh Chandra Nandi

doi:10.1002/chem.202303153

Visible Light Mediated Co-Catalyzed Isocyanide Insertion with Sulfonyl Azide: Synthesis of Sulfonyl Carbamimidic Azide and Sulfonyl Aminotetrazole via Carbodiimide Intermediate

Chemistry. 2023 Dec 22;29(72):e202303153. doi: 10.1002/chem.202303153. Epub 2023 Nov 7.

Authors

Sundaresan Ravindra¹, Kannan Natarajan¹, Vetrivel R Padma Priya¹, Ramesh Kataria², Ganesh Chandra Nandi¹

Affiliations

¹ Department of Chemistry, National Institute of Technology- Tiruchirappalli, Tiruchirappalli, Tamilnadu, 620 015, India.
² Department of Chemistry and Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India.

PMID: 37878800
DOI: 10.1002/chem.202303153

Abstract

Herein, we report an operationally simple and efficient protocol to prepare sulfonyl carbamimidic azide and N-sulfonyl aminotetrazole via Co-catalyzed three component coupling of sulfonyl azide (acts as nitrene source), isocyanide, and TMS-azide at room temperature under visible light. Initially, the carbamimidic azide is formed, which cyclizes only in the presence of base to deliver N-sulfonyl aminotetrazole in very good yields. The sulfonyl aminotetrazole can also be synthesized directly without isolating the carbamimidic azide in the presence of base. The sulfonyl azide is anticipated to generate nitrene and reacts with isocyanide to produce carbodiimide. Subsequent addition of azide (TMS-N₃ ) to carbodiimide results in the formation of carbamimidic azide.

Keywords: Aminotetrazole; Carbodiimide; Nitrene; Sulfonyl azide; carbamimidic azide.