Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with o-Bromobenzyl Alcohols through Multiple Carbon-Carbon Bond Formations

The Journal of Organic Chemistry
Masayuki IwasakiYasushi Nishihara

Abstract

A palladium-catalyzed benzannulation with o-bromobenzyl alcohols enabled the facile construction of phenanthrene skeletons via the sequential multiple carbon-carbon bond formations. A variety of multisubstituted phenanthrenes were synthesized by the reaction of (Z)-β-halostyrenes with o-bromobenzyl alcohols as well as by the three-component coupling of alkynes, aryl bromides, and o-bromobenzyl alcohols. The electron-deficient phosphine ligand played an important role to control the sequential oxidative addition of two different organic halides employed, which realized the selective formation of the desired phenanthrenes in good yields. This synthetic protocol was also applicable to the synthesis of the highly fused polycyclic aromatic hydrocarbons such as tetraphenes.

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Citations

Mar 16, 2019·Organic & Biomolecular Chemistry·Juan SongYan Qian
Dec 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hamid Azizollahi, José-Antonio García-López
Sep 11, 2019·Organic Letters·Yao ZhouQiuling Song
Jul 9, 2020·Chemical Reviews·Marius D R Lutz, Bill Morandi
May 23, 2018·Journal of the American Chemical Society·Shunsuke OnoderaFumitoshi Kakiuchi

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