Synthesis of phenanthrene derivatives via microwave-promoted Suzuki-Miyaura coupling/aldol condensation cascade reaction

ORGN 567

Jung-Nyoung Heo, heojn@krict.re.kr1, Young Ha Kim, chemisthaha@naver.com2, and Bum Tae Kim, btkim@krict.re.kr1. (1) Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, 100 Jang-dong, Yuseong-ku, Daejeon, 305-600, South Korea, (2) Department of Chemistry, Chungnam National University, 220 Gung-dong, Yuseong-ku, Daejeon, 305-764, South Korea
We have developed an efficient cascade reaction, a Suzuki-Miyaura coupling followed by an intramolecular aldol condensation, under microwave irradiation for the rapid construction of phenanthrene derivatives. For instance, reaction of methyl 2-bromphenylacetamide with 2-formylphenylboronic acid in the presence of a suitable palladium catalyst and a base provided the biaryl intermediate, which was sequentially cyclized to afford the corresponding phenanthrene in high yield.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007