ChemInform Abstract: Iron‐Catalyzed N‐Arylsulfonamide Formation Through Directly Using Nitroarenes as Nitrogen Sources.

Abstract

Iron-Catalyzed N-Arylsulfonamide Formation Through Directly Using Nitroarenes as Nitrogen Sources. -Nitromethane as well as sodium benzylsulfinate do not react. -(ZHANG, W.; XIE, J.; RAO, B.; LUO*, M.; J. Org. Chem. 80 (2015) 7, 3504-3511, http://dx.doi.org/10.1021/acs.joc.5b00130 ; Key Lab. Green Chem. Technol., Sichuan Univ., Chengdu, Sichuan 610064, Peop. Rep. China; Eng.) -M. Tismer 34-115

Highly Selective and Catalytic C–N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight

“…N-(3,4-Dihydronaphthalen-2-ylmethyl)-4-methyl-N-phenylbenzenesulfonamide (1d). Prepared according to general procedure II; 89% yield; off-white solid; mp = 130−132 °C; 4-Methyl-N-phenyl-benzenesulfonamide (3a): 25 Prepared according to general procedure IV using 4a (100 mg, 0.25 mmol, 1.0 equiv); white solid (59 mg, 95% yield). All spectroscopic data are identical to 3a obtained from 1d and those reported in the literature.…”

“…All spectroscopic data are identical to 3a obtained from 1d and those reported in the literature. 9, 148.4, 143.4, 137.8, 136.3, 135.9, 129.54 (3C), 129.52 (2C), 128.8 (2C), 128.5, 127.8, 121.0, 111.6, 110.7, 55.9, 55.8, 54.6, 21.6, 21. 7, 143.4, 140.0, 138.1, 136.5, 135.3, 132.1, 129.6 (2C), 128.2, 128.0 (3C), 127.9, 126.9, 121.9, 112.5, 110.6, 55.8 (2C), 55.7, 21.7, 21.1, 18.4 148.7, 143.9, 140.2, 135.3, 134.2, 129.8, 129.7 (2C), 129.1, 128.1, 127.8 (2C), 127.7, 127.3, 121.1, 111.6, 110.8, 55.9, 55.8, 54.4, 21.6 9, 148.7, 148.5, 148.3, 143.5, 135.9, 131.7, 129.5 (2C), 128.6, 127.9 (2C), 121.5, 121.3, 112.9, 111.8, 110.7, 110.6, 55.9 (4C) 4-Methyl-N-phenyl-benzenesulfonamide (3a): 25 Prepared according to general procedure IV using 4f (100 mg, 0.27 mmol, 1.0 equiv); white solid (60 mg, 89% yield). All data are similar to the compound obtained from 4a.…”

“…N-(2,4-Dimethyl-phenyl)-N-(4-methoxy-benzyl)-4-methylbenzenesulfonamide (4g): Prepared according to general procedure II; 80% yield; off-white solid; mp = 110−112 °C; N-(4-Fluoro-phenyl)-4-methyl-benzenesulfonamide (3f). 28 Prepared according to general procedure IV using 4i (100 mg, 0.26 mmol, 1.0 equiv); white solid (65 mg, 94% yield); 4-Methyl-N-phenyl-benzenesulfonamide (3a): 25 Prepared according to general procedure IV using 4j (100 mg, 0.28 mmol, 1.0 equiv); white solid (63 mg, 89% yield). All data are similar to the compound obtained from 4a.…”

“…7.58−7.45 (m, 3H), 7.14−7.12 (m, 3H), 6.94−6.92 (m, 2H), 6.62−6.60 (m, 2H), 6.56−6.54 (m, 1H), 4.73 (s, 2H), 3.78 (s, 3H), 3.63 (s, 3H); 13 C NMR (CDCl 3 , 100 MHz): δ 148. 7, 148.5, 138.6, 134.5 134.4, 134.3, 131.1, 129.7 (2C), 128.9 (4C), 128.5, 128.0 (2C), 126.9, 125.6, 124.2, 121.3, 111.7, 110.6, 55.9, 55.7, 55. 5, 134.8, 134.3, 134.1, 130.5, 129.4, 129.3 (3C), 128.7, 128.2, 127.0, 125.3, 124.3, 124.2, 121.5 6, 148.7, 142.5, 138.4, 129.2 (3C), 129.1 (2C), 128.4, 128.2 (3C), 127.8, 126.2, 126.1, 121.3, 111.7, 110.8, 55.9 (2C) 4-Methyl-N-phenyl-benzenesulfonamide (3a): 25 Prepared according to general procedure IV using 5a (100 mg, 0.28 mmol, 1.0 equiv); white solid (55 mg, 81% yield). All data are similar to the compound obtained from 4a.…”

“…All data are similar to the compound obtained from 4a. 4-Methyl-N-p-tolyl-benzenesulfonamide (3b): 25 Prepared according to general procedure IV using 5b (100 mg, 0.26 mmol, 1.0 equiv); white solid (53 mg, 78% yield). All data are similar to the compound obtained from 4b.…”