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Yamamoto Coupling for the Synthesis of Benzophenes and Acene-Based Cyclooctatetraenes.

Elias C RüdigerSilke KoserFrank RomingerJan FreudenbergUwe H F Bunz
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
Two TIPS-ethynylated dibromoacenes were used in a shotgun Yamamoto-reaction with 1,2-dibromobenzene or 4,5-dibromoveratrol. Four soluble benzononaphenes/benzoundecaphenes were isolated in satisfactory yields. Examples of tetracene- and pentacene-fused tetrabenzocyclooctatetraenes also isolated from this reaction are reported. All compounds were characterized by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X-ray crystallography as well as DFT and NICS calculations.
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