50875-89-3

Basic information

• Product Name: para-iodobenzenesulfonyl azide
• Synonyms: para-iodobenzenesulfonyl azide
• CAS NO: 50875-89-3
• Molecular Weight: 309.087
• Mol File: 50875-89-3.mol

Chemical Properties

• CAS DataBase Reference: para-iodobenzenesulfonyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: para-iodobenzenesulfonyl azide(50875-89-3)
• EPA Substance Registry System: para-iodobenzenesulfonyl azide(50875-89-3)

Safety Data

• Hazardous Substances Data: 50875-89-3(Hazardous Substances Data)

Upstream product

• 98-61-3 p-Iodobenzenesulfonyl chloride 

Downstream Products

• 1448845-38-2 C₁₄H₁₆IN₃O₃S 
• 1448845-43-9 C₁₄H₁₆INO₃S 

Relevant articles and documents

Intermolecular C?H Amidation of (Hetero)arenes to Produce Amides through Rhodium-Catalyzed Carbonylation of Nitrene Intermediates

Amide bond formation is one of the most important reactions in organic chemistry because of the widespread presence of amides in pharmaceuticals and biologically active compounds. Existing methods for amides synthesis are reaching their inherent limits. Described herein is a novel rhodium-catalyzed three-component reaction to synthesize amides from organic azides, carbon monoxide, and (hetero)arenes via nitrene-intermediates and direct C?H functionalization. Notably, the reaction proceeds in an intermolecular fashion with N2 as the only by-product, and either directing groups nor additives are required. The computational and mechanistic studies show that the amides are formed via a key Rh-nitrene intermediate.

Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water

A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.

Iridium-catalyzed C-H amidation of: S -tetrazines

An efficient, selective and scalable C-H amidation of s-tetrazines under iridium(III) catalysis is reported. This reaction features a broad substrate scope, high functional group tolerance, and air and water tolerance. This reaction also shows great potential for the rapid preparation of tri- and tetra-functional building blocks, which can be applied either in bioconjugation or synthesis of DNA-encoded library.

Cobalt(II)-Catalyzed Isocyanide Insertion Reaction with Sulfonyl Azides in Alcohols: Synthesis of Sulfonyl Isoureas

A Co(II)-catalyzed isocyanide insertion reaction with sulfonyl azides in alcohols to form sulfonyl isoureas via nitrene intermediate has been developed. This protocol provides a new, environmentally friendly, and simple strategy for the synthesis of sulfonyl isourea derivatives by employing a range of substrates under mild conditions.

Sulfonylative and Azidosulfonylative Cyclizations by Visible-Light-Photosensitization of Sulfonyl Azides in THF

The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of THF as the solvent is critical for successful reactions. The proposed mechanism of radical initiation involves the photosensitized formation of a triplet sulfonyl nitrene, which abstracts a hydrogen atom from THF to give a tetrahydrofuran-2-yl radical, which then reacts with the sulfonyl azide to generate the sulfonyl radical.