3 years ago

Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes

Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes
Miriam Ackermann, Simon Woodward, Saurabh K. Ahirwar, Kevin Simpson, John Ritchie, Jonathan Shine, Björk Tyril, Laurence Burroughs, Mary Robert Garrett, Peter Woodward
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. Tetracene and not hard: A procedure is reported for the preparation of substituted tetracenes from low-cost ArCH2Cl and HOCH2C≡CCH2OH. The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701170

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