Straightforward synthesis of 2- and 2,8-substituted tetracenesTools Woodward, Simon and Ackermann, Miriam and Ahirwar, Saurabh and Burroughs, Laurence and Robert Garrett, Mary and Ritchie, John and Shine, Jonathan and Tyril, Bjork and Simpson, Kevin and Woodward, Peter (2017) Straightforward synthesis of 2- and 2,8-substituted tetracenes. Chemistry - A European Journal . ISSN 1521-3765 Full text not available from this repository.AbstractA 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.
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