Synthesis of 3-aryl-4-methyl-1,2-benzenedisulfonimides, new chiral Brønsted acids. A combined experimental and theoretical study

o-Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects

“…IR spectra were recorded on a Perkin Elmer Spectrum BX FT-IR spectrometer as solutions in CHCl 3 . o-Benzenedisulfonimide (1) 13a and (R)-(−)-4-methyl-3-(2-tolyl)-1,2-benzenedisulfonimide (19) 16 were prepared as reported in the literature. All the reagents were purchased from Sigma-Aldrich.…”

“…With only four exceptions (Table 2, entries 14, [16][17][18], where compounds 5 were not solid, the work-up was very easy and convenient. It was sufficient to add H 2 O to the crude residue, filter and wash the resulting solid with additional H 2 O and a small amount of PE on a Buchner funnel.…”

“…We have very recently reported 16 the preparation of a chiral derivative of 1, namely (R)-(−)-4-methyl-3-(2-tolyl)-1,2-benzenedisulfonimide (19, Fig. 8).…”

Benzo[c]isothiazole 2‐Oxides: Three‐Dimensional Heterocycles with Cross‐Coupling and Functionalization Potential

“…First, a metal‐catalyzed Suzuki‐type cross‐coupling was demonstrated using 3d as representative starting material. Under conditions reported by Dughera, Ghigo and co‐workers for the preparation of 7‐arylsatines, the palladium/SPhos‐catalyzed reaction of 3d with phenylboronic acid ( 9 ) in the presence of cesium fluoride afforded arylated benzo[ c ]isothiazole 2‐oxides 10 in 56% yield.…”

“…Thus, treatment of 6 with 1.0 equiv. Under conditions reported by Dughera, Ghigo and coworkers for the preparation of 7-arylsatines, [15] the 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 palladium/SPhos-catalyzed reaction of 3d with phenylboronic acid (9) in the presence of cesium fluoride afforded arylated benzo[c]isothiazole 2-oxides 10 in 56% yield. Without further isolation, compounds 8 were directly oxidized to target products 3.…”