71560-75-3

Usage

Common use

Reagent in organic synthesis

Function

Acts as a strong electrophile

Structural features

a. Two phenylsulfonyl groups attached to a propan-2-one backbone
b. Significant steric hindrance
c. High degree of electron withdrawal

Reactivity

Useful in the creation of complex organic molecules, particularly in the formation of carbon-carbon bonds

Applications

a. Important building block in the production of pharmaceuticals
b. Key component in the synthesis of agrochemicals

Versatility

Valuable tool in the field of organic chemistry

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 930-69-8 sodium thiophenolate 
• 534-07-6 1,3-Dichloroacetone 
• 64-17-5 ethanol 
• 5000-44-2 1-phenylsulfonyl-2-propanone 

Downstream Products

• 112349-93-6 5,7-bis-benzenesulfonyl-1,3-diaza-adamantan-6-one 
• 3959-23-7 benzenesulfonylacetic acid 
• 112323-83-8 3,7-diacetyl-1,5-bis-benzenesulfonyl-3,7-diaza-bicyclo[3.3.1]nonan-9-one 

Relevant academic research and scientific papers

Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C-C/C-C vs C-C/O-C bond formation

Two complementary [3 + 2] annulation protocols between 3-oxoglutarates and cyclic γ-oxy-2-cycloalkenones, simply differing on the reaction temperature, are disclosed. These domino transformations allow C-C/O-C or C-C/C-C [3 + 2] annulations at will, via an intermolecular Pd-catalyzed C-allylation/intramolecular O- or C-1,4-addition sequence, respectively. In particular, exploiting the reversibility of the O-1,4-addition step, in combination with the irreversible C-1,4-addition/decarboxylation path, the intramolecular conjugate addition step could be diverted from the kinetic (O-alkylation) to the thermodynamic path (C-alkylation) thanks to a simple temperature increase. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. This [3 + 2] C-C/O-C bond forming annulation protocol could be also extended to 1,3,5-triketones as well as 1,3-bis-sulfonylpropan-2-one bis-nucleophiles.

Solid-Phase Synthesis of Imidazo[1,2-a]pyridine Using Sodium Benzenesulfinate as a Traceless Linker

(equation presented) The preparation of the first library of imidazo[1,2-a]pyridine derivatives on a solid support is described. A sulfone linker strategy was applied in the synthesis. Key steps involved in the solid-phase synthetic procedure include (i)