An FeCl3-catalyzed highly C3-selective Friedel–Crafts alkylation of indoles with alcohols

Propargylation of aromatic compounds using Ce(OTf)3 as catalyst

“…The catalyst amount also was tested using 0.1 to 0.5 mmol, the best result was obtained using 0.3 mmol of Ce(OTf) 3 (Table 1). …”

“…1 In recent years, propargylation of aromatic compounds has been studied using Brønsted acids, 2 Lewis acids, 3 and complexes involving metals such as rhenium, 4 ruthenium, 5 and gold. 6 Lanthanide salts are often employed as catalysts in organic synthesis.…”

“…These salts have attracted scientific interest due to their low toxicity, low cost, stability, and ease of handling. 7 In view of our interest in developing new methods for reactions catalyzed by salts of cerium (III), 8 we decided to study the direct alkylation reaction of aromatic compounds with propargylic alcohols using Ce(OTf) 3 .…”

Recent advances in the iron-catalyzed C-C bond formation via polar reactions of alcohols with carbon-centered nucleophiles

“…In 2007, Jana et al [27] reported an FeCl 3 -catalyzed selective 3-C alkylation of indoles with benzylic alcohols. One year later, Huang et al [28,29] developed some interesting FeCl 3 ·6H 2 O-catalyzed intramolecular Friedel-Crafts reactions of propargylic alcohols to prepare substituted hydroisoquinolines and hydronaphthalenes.…”

Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

“…Benzylic alcohols with electron withdrawing groups such as fluoro or nitro were not reactive. 69 Alkylation of indoles using allylic, benzylic and propargylic alcohols catalyzed by FeCl 3 in MeNO 2 were reported by Jana et al 70 Later, Jana et al also described the addition of benzylic alcohols to terminal aryl alkynes catalyzed by FeCl 3 in MeNO 2 . 71 In the same year, Jana et.…”