- BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives.
BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives.
The Journal of organic chemistry (2009-10-30)
G K Surya Prakash, Chiradeep Panja, Anton Shakhmin, Eric Shah, Thomas Mathew, George A Olah
PMID19863094
ABSTRACT
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.
MATERIALI
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Supelco
Boron trifluoride - 1-butanol solution, ~10% in 1-butanol (∼1.3 M), for GC derivatization, LiChropur™