Synthesis and Chiroptical Properties of Planar Chiral Azahelicenes Based on [2.2]Paracyclophane.

Org Lett

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, 163 Xianlin Avenue, Nanjing 210023, Jiangsu, China.

Published: November 2021

Three pairs of planar chiral heteroarenes were synthesized using palladium-catalyzed Buchwald-Hartwig coupling and hypervalent iodine-mediated oxidative cyclization from optically pure 4-amino[2.2]paracyclophane. Among them, an enantiomer of planar chiral azahelicene was found to have circularly polarized luminescence activity that was remarkably stronger than that of planar chiral heteroarenes.

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http://dx.doi.org/10.1021/acs.orglett.1c03325DOI Listing

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