Literature DB >> 22394317

Access to "Friedel-Crafts-restricted" tert-alkyl aromatics by activation/methylation of tertiary benzylic alcohols.

Joshua A Hartsel1, Derek T Craft, Qiao-Hong Chen, Ming Ma, Paul R Carlier.   

Abstract

Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl(2) or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.

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Year:  2012        PMID： 22394317      PMCID： PMC3321128          DOI： 10.1021/jo202371c

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


  6 in total

1.  Highly alkyl-selective addition to ketones with magnesium ate complexes derived from Grignard reagents.

Authors:  Manabu Hatano; Tokihiko Matsumura; Kazuaki Ishihara
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

2.  Antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,1,2,2-tetraalkyl-1,2 -diphenylethanes.

Authors:  R W Hartmann; G Kranzfelder; E von Angerer; H Schönenberger
Journal:  J Med Chem       Date:  1980-08       Impact factor: 7.446

3.  Zinc(II)-catalyzed addition of Grignard reagents to ketones.

Authors:  Manabu Hatano; Orie Ito; Shinji Suzuki; Kazuaki Ishihara
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

4.  Quinoline synthesis: scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes.

Authors:  Mark Austin; Oliver J Egan; Raymond Tully; Albert C Pratt
Journal:  Org Biomol Chem       Date:  2007-10-11       Impact factor: 3.876

5.  Synthesis of aromatic compounds containing a 1,1-dialkyl-2-trifluoromethyl group, a bioisostere of the tert-alkyl moiety.

Authors:  Hirotaka Tanaka; Yuji Shishido
Journal:  Bioorg Med Chem Lett       Date:  2007-09-18       Impact factor: 2.823

6.  Towards a species-selective acetylcholinesterase inhibitor to control the mosquito vector of malaria, Anopheles gambiae.

Authors:  Paul R Carlier; Troy D Anderson; Dawn M Wong; Danny C Hsu; Joshua Hartsel; Ming Ma; Eric A Wong; Ranginee Choudhury; Polo C-H Lam; Maxim M Totrov; Jeffrey R Bloomquist
Journal:  Chem Biol Interact       Date:  2008-05-04       Impact factor: 5.192
  6 in total
  4 in total

1.  Re-engineering aryl methylcarbamates to confer high selectivity for inhibition of Anopheles gambiae versus human acetylcholinesterase.

Authors:  Joshua A Hartsel; Dawn M Wong; James M Mutunga; Ming Ma; Troy D Anderson; Ania Wysinski; Rafique Islam; Eric A Wong; Sally L Paulson; Jianyong Li; Polo C H Lam; Maxim M Totrov; Jeffrey R Bloomquist; Paul R Carlier
Journal:  Bioorg Med Chem Lett       Date:  2012-06-06       Impact factor: 2.823

2.  An Efficient Synthesis of Geminal-Dialkyl Dienes for Olefin Metathesis Polymerization.

Authors:  William J Wolf; Jiaming Li; Simon C Jones; Brian M Stoltz; Robert H Grubbs
Journal:  Macromolecules       Date:  2020-09-10       Impact factor: 5.985

3.  Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].

Authors:  Gary A Molander; Livia N Cavalcanti; Carolina García-García
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

4.  Synthesis of 1,1'-Diarylethanes and Related Systems by Displacement of Trichloroacetimidates with Trimethylaluminum.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  J Org Chem       Date:  2018-03-08       Impact factor: 4.354
  4 in total

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