Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

Abstract

A general method for the N-arylation of sulfamides with aryl bromides is described.The protocol leverages a dual-catalytic system of nickel and a photoexcitable iridium complex and proceeds at room temperature under visible light irradiation. Using these tactics, aryl boronic esters and aryl chlorides can be carried through the reaction untouched. Thereby, this method complements known Buchwald-Hartwig coupling methods for N-arylation of sulfamides.

Lewis Acid‐Catalyzed Nucleophilic Substitutions of Benzylic Alcohols with Sulfamides

“…1 H NMR (CDCl 3 ) δ = 7.42-7.36 (m, 4H), 7.36-7.29 (m, 4H), 7.27-7.21 (m, 2H), 5.23 (s, 1H), 1.87 (br s, 2H) ppm. 13 C NMR (CDCl 3 ) δ = 145. 5, 128.4, 126.83, 126.80, 59.6 ppm. [Analytical Data of Compounds 2 a-2 k, 2 m, 2 n, 6 a, 6 b, 6 d, 6 e, 7, and 8] N-(diphenylmethyl)-N',N'-dimethylsulfuric diamide (2 a) (Table 2, entry 1).…”

“…1 H NMR (CDCl 3 ) δ = 7.30-7.25 (m, 2H), 7.21-7.26 (m, 6H), 6.03 (d, J = 6.0 Hz, 1H), 4.61 (br s, 1H), 2.55 (s, 6H), 2.38 (s, 6H) ppm. 13 C NMR (CDCl 3 ) δ = 138.7, 136. 1, 130.9, 127.7, 127.4, 125.9, 55.0, 37.5, 19.2 N-[bis(3-methylphenyl)methyl]-N',N'-dimethylsulfuric diamide (2 c) (Table 2, entry 3).…”

“…1 H NMR (CDCl 3 ) δ = 7.23 (t, J = 8.0 Hz, 2H), 7.17-7.06 (m, 6H), 5.54 (d, J = 7.0 Hz, 1H), 4.91 (br s, 1H), 2.56 (s, 6H), 2.34 (s, 6H) ppm. 13 C NMR (CDCl 3 ) δ = 141. 4, 138.4, 128.5, 128.4, 128.0, 124.3, 61.5, 37.6, 21.4 N-[bis(4-methylphenyl) 6, 137.3, 129.3, 127.2, 61.1, 37.6, 21.0…”

“…1 H NMR (CDCl 3 ) δ = 7.32-7.26 (m, 6H), 7.22-7.18 (m, 2H), 5.55 (d, J = 7.5 Hz, 1H), 5.13 (br s, 1H), 2.59 (s, 6H) ppm. 13 C NMR (CDCl 3 ) δ = 142. 6, 134.8, 130.2, 128.3, 127.4, 125.5, 60.6, 37.6 (Table 2, 4, 133.8, 129.0, 128.7, 60.3, 37.6 , 1H), 4.36 (q, J = 7.0 Hz, 4H), 2.57 (s, 6H), 1.37 (t, J = 7.0 Hz, 6H) ppm.…”

“…[11] To provide symmetrical N,N'-disubstituted sulfamides, amination with SO 2 /I 2 [7d] or DABCO • (SO 2 ) 2 /I 2 , [12] which reduced the difficulty of handling harmful SO 2 gas, has also been reported (Scheme 1d). In addition, the transition-metal catalyzed coupling reaction (Scheme 1e), [13] reductive amination of aldehydes, [14] and 1,2-diamination of alkenes [15] have also been performed for the synthesis of sulfamides.…”