N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• ) by using an organocatalyst was reported by Wang and co-workers (Scheme 35) [67]. Several orgnocatalysts, such as piperidine, and pyrrolidine derivatives were evaluated for the coupling reaction, in which pyrrolidine trifluoromethanesulfonamide A was selected as the best catalyst for this purpose. It

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

• chloromethylthiirane (epithiochlorohydrin, 398a), with hard and weak nucleophiles [105][106][107][108][109], including phenoxides [105], carboxylates and dicarboxylates [106][107], potassium cyanide, sodium azide, hydroxylamine, trifluoromethanesulfonamide, and pyridine [108]. However, the method could only applied to

Synthesis and stability of strongly acidic benzamide derivatives

• Frederik Diness,
• Niels J. Bjerrum and
• Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

• trifluoromethanesulfonamide group are reported. Novel derivatives of these types of acids were synthesized in good yields. The generated N-triflylbenzamides were further functionalized through cross-coupling and nucleophilic aromatic substitution reactions. All compounds were stable in dilute aqueous solutions. Studies of

• stability under acidic and basic conditions are also reported. Keywords: benzoic acid; cross-coupling; hydrolysis; SNAr; trifluoromethanesulfonamide; Introduction Very strong organic acids are interesting as catalysts for chemical reactions [1][2] and for facilitation of proton conduction [3]. In order to

• trifluoromethanesulfonamide (1) group [9][10][11]. Interestingly, these types of compounds have attracted little attention and have not thoroughly been explored with regards to their applications. Few publications report the application of N-triflylbenzamides as benzoic acid bioisosteres in receptor antagonists and enzyme

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF₃SO₂Cl

• Hélène Chachignon,
• Hélène Guyon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2800–2818, doi:10.3762/bjoc.13.273

• trifluoromethanesulfonamide (triflamide) derivatives, which are used in drugs and agrochemicals [3]. The C-trifluoromethylsulfonylation is less reported than the corresponding O- and N-trifluoromethylsulfonylations, although the resulting triflone group is an important synthetic tool for further functionalisation [4][5

Synthesis of guanidinium–sulfonimide ion pairs: towards novel ionic liquid crystals

• Martin Butschies,
• Manuel M. Neidhardt,
• Markus Mansueto,
• Sabine Laschat and
• Stefan Tussetschläger

Beilstein J. Org. Chem. 2013, 9, 1093–1101, doi:10.3762/bjoc.9.121

• [38], which was treated with trifluoromethanesulfonamide (5a) in the presence of NEt3 following a procedure by Hesemann and Brunel [40]. Then the fluorinated sulfonimide was converted to the potassium salt 6a after recrystallization from MeOH in 60% yield (Scheme 2). The corresponding nonfluorinated

• File 1, Table S2). 4-(Dodecyloxy)-N-((trifluoromethyl)sulfonyl)benzenesulfonamide, potassium salt (6a): A mixture of trifluoromethanesulfonamide (5a) (207 mg, 1.38 mmol) and 4-(dodecyloxy)-benzenesulfonylchloride (4) (500 mg, 1.39 mmol) was dissolved in abs dichloromethane (20 mL). Abs triethylamine (1