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

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, th...

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Bibliographic Details
Published in:	Chemistry : a European journal Vol. 29; no. 72; pp. e202303153 - n/a
Main Authors:	Ravindra, Sundaresan, Natarajan, Kannan, Padma Priya, Vetrivel R., Kataria, Ramesh, Nandi, Ganesh Chandra
Format:	Journal Article
Language:	English
Published:	Germany Wiley Subscription Services, Inc 22-12-2023
Subjects:	Aminotetrazole carbamimidic azide Carbodiimide Chemistry Nitrene Room temperature Sulfonyl azide carbamimidic azide Nitrene Aminotetrazole Sulfonyl azide Carbodiimide
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Summary:	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. We report an efficient protocol to prepare sulfonyl carbamimidic azide and 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. The sulfonyl carbamimidic azide cyclizes in the presence of base to deliver N‐sulfonyl aminotetrazole, which can also be synthesized directly without isolating the sulfonyl carbamimidic azide.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.202303153