Pd-Catalyzed one-pot dehydroxylative coupling of phenols with K₄[Fe(CN)₆] mediated by SO₂F₂: a practical method for the direct conversion of phenols to aryl nitriles

Abstract

A SO2F2 mediated Pd-catalyzed one-pot dehydroxylative cyanation of phenols to aryl nitriles was accomplished by employing (K4[Fe(CN)6]) as the cyanating reagent.

SO2F2-Mediated Epoxidation of Olefins with Hydrogen Peroxide

“…2,6-b′]bisoxirene (2h). 2e colorless solid; mp 179−181 °C; 63 mg, 85%; 1 H NMR (400 MHz, CDCl 3 ) δ 3.50 (s, 1H), 3.37 (d, J = 2.5 Hz, 1H), 3.23 (d,J = 3.4 Hz,1H),3.19 (d,J = 3.5 Hz,1H),2.65 (d,J = 4.4 Hz,1H),2.57 (dd,J = 8.2,4.4 Hz,1H),2.46 (d,J = 3.4 Hz,2H),1.87 (dd,J = 15.4,8.8 Hz,1H),1H),1H),0.82 (d,1H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 61.…”

“…9,55.6,55.5,52.4,52.4,52.3,52.2,51.6,51.5,50.9,50.8,46.1,46.0,45.6,oxirane (2j). 19 colorless oil; 61 mg, 61%; 1 H NMR (400 MHz, CDCl 3 ) δ 7.46 (dd, J = 8.4, 2.0 Hz, 2H), 7.14 (d,J = 7.9 Hz,2H),1H), 3.13 (dt, J = 5.5, 2.9 Hz, 1H), 2.74 (dt, J = 5.5, 2.2 Hz, 1H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 136.…”

Synthesis of N-Acyl Sulfamates from Fluorosulfonates and Potassium Trimethylsilyloxyl Imidates

“…Fluorosulfate was first reported in 1990s. − Its chemistry, however, was relatively unexplored until the Sharpless group reported the robust synthesis of (hetero)­aryl fluorosulfonates in 2014, which sparked a surge in investigation of the chemistry of fluorosulfonate for medicinal, biological, and material applications. − Currently, as an emerging class of electrophiles, fluorosulfonate has already shown great versatility in various chemical transformations ranging from conventional organic synthesis to biocompatible click chemistry, i.e., cross-coupling reactions, − C–H activation reactions, , late-stage drug functionalization, − and sulfur­(VI) fluoride exchange (SuFEx)-based click chemistry. − …”

Installation of sulfonyl fluorides onto primary amides

“…Sulfur(VI) fluoride exchange (SuFEx), is a new class of click chemistry developed by Professor K. B. Sharpless and coworkers in 2014, for creating molecular connections based on the unique stability-reactivity pattern of S VI -F bond with absolute reliability and unprecedented efficiency, which has been widely applied in organic synthesis, chemical biology and drug discovery [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Among all the developed S(VI)-F species, sulfonyl fluoride (RSO2F) was specifically recognized as unique scaffold for covalent protein inhibitors and biological probes with the affinity-driven activation for forming covalent linkages with the amino acid residues of protein binding sites (Figure 1) [20].…”