Synthesis of a Bent, Twisted, and Chiral Phenanthrene via an Iodine Monochloride-Mediated, Strain-Inducing π-Extension Reaction
2022
Saha, Nirob K. | Barnes, Timothy H. | Wilson, Laura J. | Merner, Bradley L.
A strategy for the synthesis of substituted and strained p-phenylene units is reported. An oxidative allylic alcohol rearrangement, followed by organometallic addition to the resulting α-ketol and subsequent dehydrative aromatization, affords p-terphenyl-containing macrocycles in which the central p-phenylene has been selectively substituted. Ten 18-membered macrocycles have been synthesized, eight of which contain substituents that could enable π-extension. Only alkynylated derivatives were amenable to π-extension via an ICl-mediated reaction, affording a highly bent, twisted, and chiral phenanthrene.
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