10.1002/anie.201712783
Angewandte Chemie International Edition
COMMUNICATION
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Scheme 7: Relative stabilities of benzanthrene derivatives where X = SnMe3,
at (U)M06-2X/LanL2DZ level at 110°C, in kcal/mol. Experimentally observed
products are boxed.
In conclusion, peri-cyclizations of acene subunits and vinyl
radicals formed from propargylic ethers provide a viable strategy
for benzannulation at the L-region of acenes. The initially formed
cyclic products can be trapped via a reductive or oxidative path
with the concomitant loss of the alkoxy directing group. The
Bu3Sn-moeity can be retained or exchanged to give iodoarenes
for further cross-coupling transformations on route to extended
polyaromatics.
Acknowledgement: We are grateful for the support of the
National Science Foundation (Grant CHE-035678) and for the
assistance of the FSU Research Computing Center.
Author Information
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*alabugin@chem.fsu.edu
Keywords: alkyne benzannulation • radical cyclizations•
polyaromatics • zigzag edge• L-region
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