Direct one-pot synthesis of phenanthrenes via Suzuki-Miyaura coupling/aldol condensation cascade reaction.
We have developed an efficient cascade reaction, a Suzuki-Miyaura coupling followed by an aldol condensation, for the construction of phenanthrene derivatives using microwave irradiation. For example, the reaction of methyl 2-bromophenylacetamide with 2-formylphenylboronic acid in the presence of a palladium catalyst and a base provided a biaryl intermediate, which underwent in situ cyclization to afford the corresponding phenanthrene in high yield.
D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry* / Q000528:radiation effects; D008872:Microwaves; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D013237:Stereoisomerism
D007659:Ketones; D009942:Organometallic Compounds; D010616:Phenanthrenes; D010165:Palladium