BF3−H2O Catalyzed Hydroxyalkylation of Aromatics with Aromatic Aldehydes and Dicarboxaldehydes: Efficient Synthesis of Triarylmethanes, Diarylmethylbenzaldehydes, and Anthracene Derivatives

• Published in: Journal of organic chemistry Vol. 74; no. 22; pp. 8659 - 8668
• Main Authors: Prakash, G. K. Surya, Panja, Chiradeep, Shakhmin, Anton, Shah, Eric, Mathew, Thomas, Olah, George A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 20.11.2009; Amer Chemical Soc
• Subjects: Aldehydes - chemical synthesis; Aldehydes - chemistry; Alkylation; Anthracenes - chemical synthesis; Anthracenes - chemistry; Boranes - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Condensed benzenic and aromatic compounds; Exact sciences and technology; General and physical chemistry; Hydrocarbons, Aromatic - chemistry; Methane - analogs & derivatives; Methane - chemical synthesis; Methane - chemistry; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Water - chemistry; ACID; BENZALDEHYDE; BENZENE; PHENYL CATION; ORGANIC-REACTIONS; BORON FLUORIDE; CONDENSATION; IONS; POTASSIUM-NITRATE; Water; Terphenyl derivatives; Arene; Catalytic reaction; Dialdehyde; Hydroxyalkylation; Strong acid; Aldehyde; Anthracene derivatives; Superacid; Benzenic compound; Aromatic compound; Chemical synthesis; Catalyst; Benzaldehyde derivatives
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo901668j

BF3-monohydrate is found to be an efficient and strong acid catalyst as well as an effective protosolvating medium suitable for the hydroxyalkylation of arenes with aromatic aldehydes. This reaction has been extended to aromatic dialdehydes, such as terephthalic dicarboxaldehyde and isoterephthalic dicarboxaldehyde, for the efficient synthesis of diarylmethylbenzaldehydes, which are useful synthons for various organic transformations. Further, successful one step convergent synthesis of various synthetically useful anthracene derivatives from phthalaldehyde was also achieved. BF3−H2O is less expensive and acts as an efficient substitute for nonoxidizing strong protic acids/superacids.