BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives.
BF(3)-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. BF(3)-H(2)O is less expensive and acts as an efficient substitute for nonoxidizing strong protic acids/superacids.
Prakash
G K Surya
GK
Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, California 90089-1661, USA. gprakash@usc.edu
Panja
Chiradeep
C
Shakhmin
Anton
A
Shah
Eric
E
Mathew
Thomas
T
Olah
George A
GA
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D000478:Alkylation; D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D000873:Anthracenes; D001880:Boranes; D006841:Hydrocarbons, Aromatic; D014867:Water; C021274:boron trifluoride; C034020:anthracene; D008697:Methane