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Synthesis of 2-Phospha[7]helicene, a Helicene with a Terminal Phosphinine Ring
Organic Letters  (IF6.072),  Pub Date : 2022-06-24, DOI: 10.1021/acs.orglett.2c01723
Tomáš Beránek, Martin Jakubec, Jan Sýkora, Ivana Císařová, Jaroslav Žádný, Jan Storch

A synthetic strategy toward phosphahelicenes containing a terminal phosphinine ring has been explored. The 4-phenyl-6-methyl-2-phospha[7]helicene was prepared from starting 2-bromobenzo[c]phenanthrene in 12% overall yield in 12 steps. The synthetic approach involves introduction of the phosphorus function prior to photocyclization forming the final helicene skeleton, followed by the formation of a phosphorus hexacycle. The structure of the first phosphahelicene with a terminal phosphinine ring was confirmed by X-ray crystallography.