61128-12-9Relevant academic research and scientific papers
Redox-Neutral Organometallic Elementary Steps at Bismuth: Catalytic Synthesis of Aryl Sulfonyl Fluorides
Cornella, Josep,Magre, Marc
supporting information, p. 21497 - 21502 (2022/01/03)
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.
SULFONATION OF CUMENE WITH SULFURIC AND HALOGENOSULFONIC ACIDS
Krylov, E.N.,Odintsova, G.N.
, p. 1695 - 1701 (2007/10/02)
The sulfonation of cumene by sulfuric and chloro- and fluorosulfonic acids in the range of 0-100 deg C under heterogenous and heterogenous-homogenous conditions gives mixtures of isomeric sulfonyl halides and/or sulfonic acids, in which the para isomer predominates (90-95percent of the total isomers at temperatures above 75 deg C and/or with the addition of the sulfonating agent to the cumene).If the reagents are mixed in the opposite order and at low temperatures (0-25 deg C), the proportion of the ortho isomer in the mixture of sulfo products increases to 20-22percent.The yield of the sulfonyl halides show an extremal relationship with temperature.The composition of the sulfonic acids and their halides formed under the conditions of a single experiment with the halogenosulfonic acids differ as a result, probably, of the nonequilibrium nature of the process and of the presence of several paths to the formation of the acid halides.
