2, 6‐Bis(amido)benzoic Acid with Internal Hydrogen Bond as Brønsted Acid Catalyst for Friedel–Crafts Reaction of Indoles. Issue 9 (15th June 2015)

• Record Type: Journal Article
• Authors: Moriyama, Katsuhiko; Sugiue, Toru; Saito, Yuki; Katsuta, Shoichi; Togo, Hideo
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 9(2015)
• Page Start: 2143
• Page End: 2149
• Publication Date: 2015-06-15
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201401189
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Benzoic acid catalysts bearing two amide groups that increase the Brønsted acidity of the carboxylic acid moiety by internal hydrogen‐bonding interactions were designed as a novel class of carboxylic acid catalysts for the Friedel–Crafts reaction of indoles with β‐nitrostyrenes and 3, 3‐disubstituted 3<italic>H</italic>‐indoles to obtain the corresponding Friedel–Crafts adducts in high yields. The internal hydrogen‐bonding benzoic acid catalysts have a relatively high Brønsted acidity compared with benzoic acid based on the p<italic>K</italic>_a measurements in DMSO by UV spectrophotometric titration.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj10cp20g5" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>