366-85-8

Basic information

• Product Name: 4-(ethoxycarbonyl)-benzenesulfonyl fluoride
• Synonyms: 4-(ethoxycarbonyl)-benzenesulfonyl fluoride
• CAS NO: 366-85-8
• Molecular Weight: 232.232
• Mol File: 366-85-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4-(ethoxycarbonyl)-benzenesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(ethoxycarbonyl)-benzenesulfonyl fluoride(366-85-8)
• EPA Substance Registry System: 4-(ethoxycarbonyl)-benzenesulfonyl fluoride(366-85-8)

Safety Data

• Hazardous Substances Data: 366-85-8(Hazardous Substances Data)

Upstream product

• 4334-88-7 p-ethoxycarbonylphenylboronic acid 
• 64-17-5 ethanol 
• 455-26-5 4-carboxybenzenesulfonyl fluoride 
• 10130-89-9 p-carboxyphenylsulfonyl chloride 
• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 94-09-7 p-aminoethylbenzoate 
• 10486-51-8 4-ethoxycarbonylbenzenesulfonyl chloride 
• 402-55-1 4-fluorosulfonylbenzoyl chloride 

Relevant articles and documents

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides

A Bi-catalyzed synthesis of sulfonyl fluorides from the corresponding (hetero)aryl boronic acids is presented. We demonstrate that the organobismuth(III) catalysts bearing a bis-aryl sulfone ligand backbone revolve through different canonical organometallic steps within the catalytic cycle without modifying the oxidation state. All steps have been validated, including the catalytic insertion of SO2 into Bi-C bonds, leading to a structurally unique O-bound bismuth sulfinate complex. The catalytic protocol affords excellent yields for a wide range of aryl and heteroaryl boronic acids, displaying a wide functional group tolerance.

Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts

The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper-free Sandmeyer-type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N-fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.