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

Woodward, Simon; Ackermann, Miriam; Ahirwar, Saurabh; Burroughs, Laurence; Robert Garrett, Mary; Ritchie, John; Shine, Jonathan; Tyril, Bjork; Simpson, Kevin; Woodward, Peter

Authors

Simon Woodward

Miriam Ackermann

Saurabh Ahirwar

Laurence Burroughs

Mary Robert Garrett

John Ritchie

Jonathan Shine

Bjork Tyril

Kevin Simpson

Peter Woodward



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.

Journal Article Type Article
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
APA6 Citation Woodward, S., Ackermann, M., Ahirwar, S., Burroughs, L., Robert Garrett, M., Ritchie, J., …Woodward, P. (in press). Straightforward synthesis of 2- and 2,8-substituted tetracenes. Chemistry - A European Journal, doi:10.1002/chem.201701170
DOI https://doi.org/10.1002/chem.201701170
Keywords acenes; aldehydes; arenes; aromaticity; Bradsher cyclization; C−C coupling
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201701170/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
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.wi...02/chem.201701170/full. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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