Literature DB >> 19863094

BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives.

G K Surya Prakash1, Chiradeep Panja, Anton Shakhmin, Eric Shah, Thomas Mathew, George A Olah.   

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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Year:  2009        PMID: 19863094     DOI: 10.1021/jo901668j

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  8 in total

1.  Superelectrophiles and the effects of trifluoromethyl substituents.

Authors:  Matthew J O'Connor; Kenneth N Boblak; Michael J Topinka; Patrick J Kindelin; Jason M Briski; Chong Zheng; Douglas A Klumpp
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

2.  Utilization of the hydroxyalkylation reaction to prepare bis(benzocrown ethers).

Authors:  Matthew Zielinski; Adam F Tracy; Douglas A Klumpp
Journal:  Tetrahedron Lett       Date:  2012-02-02       Impact factor: 2.415

Review 3.  Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides.

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4.  BF3-etherate promoted facile access to vinyloxyimidazopyridines: a metal-free sustainable approach.

Authors:  Saurabh Kumar Tiwari; Mohd Nazeef; Ankit Verma; Ankit Kumar; Vikas Yadav; Neetu Yadav; Saif Ansari; I R Siddiqui
Journal:  Mol Divers       Date:  2021-05-16       Impact factor: 2.943

5.  Metal- and solvent-free synthesis of aniline- and phenol-based triarylmethanes via Brönsted acidic ionic liquid catalyzed Friedel-Crafts reaction.

Authors:  Nipaphorn Ponpao; Warapong Senapak; Rungnapha Saeeng; Jaray Jaratjaroonphong; Uthaiwan Sirion
Journal:  RSC Adv       Date:  2021-06-30       Impact factor: 4.036

6.  Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

Authors:  Baosheng Wei; Qianyi Ren; Thomas Bein; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-17       Impact factor: 15.336

7.  Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products.

Authors:  Dmitry S Ryabukhin; Dmitry N Zakusilo; Mikhail O Kompanets; Anton A Tarakanov; Irina A Boyarskaya; Tatiana O Artamonova; Mikhail A Khohodorkovskiy; Iosyp O Opeida; Aleksander V Vasilyev
Journal:  Beilstein J Org Chem       Date:  2016-10-05       Impact factor: 2.883

8.  A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids.

Authors:  Oksana S Mikhalchenko; Dina V Korchagina; Konstantin P Volcho; Nariman F Salakhutdinov
Journal:  Beilstein J Org Chem       Date:  2016-04-06       Impact factor: 2.883

  8 in total

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