124397-36-0Relevant academic research and scientific papers
One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides
Davies, Alyn T.,Curto, John M.,Bagley, Scott W.,Willis, Michael C.
, p. 1233 - 1237 (2017)
A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.
Synthesis of Sulfonyl Azides via Lewis Base Activation of Sulfonyl Fluorides and Trimethylsilyl Azide
Barrow, Andrew S.,Moses, John E.
supporting information, p. 1840 - 1843 (2016/07/16)
A protocol for the efficient conversion of sulfonyl fluorides into sulfonyl azides through Lewis base activation is described. The in situ generated sulfonyl azides are efficient diazo-transfer agents, affording diazo compounds and primary azides in excellent yields.
Correlation of Carbon-13 Substituent-Induced Chemical Shifts: meta- and para-Substituted Methyl Benzoates
Budesinsky, Milos,Exner, Otto
, p. 585 - 591 (2007/10/02)
Carbon-13 NMR spectra are reported for 69 substituted methyl benzoates in deuteriochloroform or in its mixture with dimethyl sulphoxide-d6.The substituent-induced chemical shifts (SCS) of the CO carbon correlate poorly with dual substituent parameters (DSP) in all possible modifications, and for meta derivatives in particular this correlation is both overparameterized and imprecise.A much better correlation was obtained with parameters (designated Bm, Bp and Cp) derived previously by principal component analysis (PCA) from a larger set.The SCS of the CH3 carbon correlate very well with the original simple Hammett equation, and no DSP treatment is needed.The clustering of substituents is not consequential in such a large set.KEY WORDS Methyl benzoates 13C NMR Substituent effects
