Straightforward synthesis of 2- and 2,8-substituted tetracenes

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Woodward, Simon, Ackermann, Miriam, Ahirwar, Saurabh, Burroughs, Laurence, Robert Garrett, Mary, Ritchie, John, Shine, Jonathan, Tyril, Bjork, Simpson, Kevin and Woodward, Peter (2017) Straightforward synthesis of 2- and 2,8-substituted tetracenes. Chemistry - A European Journal . ISSN 1521-3765

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Abstract

A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)- 1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1 = Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2- Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2 = Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2- Ar1CH2(CHO)C=C(CHO)CH2Ar2 which in many cases undergo titanium(IV) chloride induced double Bradsher closure providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out.

Item Type: Article
RIS ID: https://nottingham-repository.worktribe.com/output/861387
Additional Information: This is the peer reviewed version of the following article: Woodward, S., Ackermann, M., Ahirwar, S. K., Burroughs, L., Garrett, M. R., Ritchie, J., Shine, J., Tyril, B., Simpson, K. and Woodward, P. (2017), Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes. Chem. Eur. J which has been published in final form at http://onlinelibrary.wiley.com/wol1/doi/10.1002/chem.201701170/full. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Keywords: acenes; aldehydes; arenes; aromaticity; Bradsher cyclization; C−C coupling
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/chem.201701170
Depositing User: Smith, Ruth
Date Deposited: 05 May 2017 13:26
Last Modified: 04 May 2020 18:46
URI: https://eprints.nottingham.ac.uk/id/eprint/42527

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