Regioselective C5-H direct iodination of indoles

Abstract

An efficient highly regioselective C5-H direct iodination of indoles is reported herein for the first time. Due to the versatility of aryl iodides, the method offers a general and practical...

Visible‐Light‐Driven Sulfonylation/Cyclization to Access Sulfonylated Benzo[4,5]imidazo[2,1‐a]isoquinolin‐6(5H)‐ones

“…In photoredox transformations containing sulfonyl chlorides, a major process is to develop C−C bond after the loss of SO 2 , the methods on the formation of C−S bond are very rare [22] . Sulfone functional groups with great synthetic potential are widely used in the fields of agrochemicals and natural product synthesis, and many sulfonyl‐functionalized compounds have excellent biological properties [23–33] . Herein, we reported a new and efficient visible‐light‐induced sulfonylation/cyclization reaction that used the sulfonyl chloride as the sulfonylation reagent and oxidant to promote the reaction, leading to a series of sulfonylated benzimidazo[2,1‐ a ]isoquinolin‐6(5 H )‐ones under mild reaction conditions (Scheme 1,d).…”

Forging C−S(Se) Bonds by Nickel‐catalyzed Decarbonylation of Carboxylic Acid and Cleavage of Aryl Dichalcogenides

“…(4‐(Tert‐butyl)phenyl)(4‐methoxyphenyl)sulfane (4 g) [27] The title compound was isolated by column chromatography (petroleum ether) as a colorless oil (117 mg, 86 % yield). 1 H NMR (400 MHz, CDCl 3 ) δ 7.39 (d, J =7.9 Hz, 2H), 7.28–7.23 (m, 2H), 7.13 (d, J =7.6 Hz, 2H), 6.88 (d, J =7.8 Hz, 2H), 3.80 (s, 3H), 1.28 (s, 9H).…”

“…4‐((4‐Methoxyphenyl)thio)benzonitrile (4 r) [27] The title compound was isolated by column chromatography (eluent: EtOAc/petroleum ether=1/30) as a white solid (115 mg, 95 % yield). mp 102.5‐103.6 °C.…”

Recent Trends in Nickel‐Catalyzed C−S Bond Formation

“…The direct making of C−S bond of aryl sulfides using arylsulfonyl chlorides and aryl iodides via Ni catalyst using Mn as a reducing agent were reported [88] . Various unsymmetrical aryl sulfides were made using this procedure in moderate to good yields.…”

“…The direct making of CÀ S bond of aryl sulfides using arylsulfonyl chlorides and aryl iodides via Ni catalyst using Mn as a reducing agent were reported. [88] Various unsymmetrical aryl sulfides were made using this procedure in moderate to good yields. In (15 mol%) as ligand, Mn dust as the reducing agent, as the additive sodium iodide and potassium fluoride, in N,N-dimethylformamide solvent in N 2 atmosphere gives the best result with a yield of the product 92%.…”