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BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives.
J Org Chem. 2009 Nov 20; 74(22):8659-68.JO

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Prakash 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 C
No affiliation info available
Shakhmin A
No affiliation info available
Shah E
No affiliation info available
Mathew T
No affiliation info available
Olah GA
No affiliation info available

MeSH

AldehydesAlkylationAnthracenesBoranesCatalysisHydrocarbons, AromaticMethaneMolecular StructureStereoisomerismWater

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19863094

Citation

Prakash, G K Surya, et al. "BF3-H2O Catalyzed Hydroxyalkylation of Aromatics With Aromatic Aldehydes and Dicarboxaldehydes: Efficient Synthesis of Triarylmethanes, Diarylmethylbenzaldehydes, and Anthracene Derivatives." The Journal of Organic Chemistry, vol. 74, no. 22, 2009, pp. 8659-68.
Prakash GK, Panja C, Shakhmin A, et al. BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives. J Org Chem. 2009;74(22):8659-68.
Prakash, G. K., Panja, C., Shakhmin, A., Shah, E., Mathew, T., & Olah, G. A. (2009). BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives. The Journal of Organic Chemistry, 74(22), 8659-68. https://doi.org/10.1021/jo901668j
Prakash GK, et al. BF3-H2O Catalyzed Hydroxyalkylation of Aromatics With Aromatic Aldehydes and Dicarboxaldehydes: Efficient Synthesis of Triarylmethanes, Diarylmethylbenzaldehydes, and Anthracene Derivatives. J Org Chem. 2009 Nov 20;74(22):8659-68. PubMed PMID: 19863094.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives. AU - Prakash,G K Surya, AU - Panja,Chiradeep, AU - Shakhmin,Anton, AU - Shah,Eric, AU - Mathew,Thomas, AU - Olah,George A, PY - 2009/10/30/entrez PY - 2009/10/30/pubmed PY - 2010/1/23/medline SP - 8659 EP - 68 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 22 N2 - 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. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19863094/BF3_H2O_catalyzed_hydroxyalkylation_of_aromatics_with_aromatic_aldehydes_and_dicarboxaldehydes:_efficient_synthesis_of_triarylmethanes_diarylmethylbenzaldehydes_and_anthracene_derivatives_ L2 - https://doi.org/10.1021/jo901668j DB - PRIME DP - Unbound Medicine ER -