An efficient method for synthesis of 4-bromo-12- benzophenone-imine [2,2]paracyclophane by using Hartwig-Buchwald reaction

ORGN 543

Yudao Ma, ydma@sdu.edu.cn1, Tong Zhou, ydma@sdu.edu.cn1, Xi Fang, ydma@sdu.edu.cn1, Changqin Ma, ydma@sdu.edu.cn1, Qiang Chai, qiangchai@hotmail.com2, Minghu Huang, huangmhhjy@yahoo.com.cn1, Xueying Liu, ydma@sdu.edu.cn1, and Chun Song, chunsong@sdu.edu.cn3. (1) Chemistry Department, Shandong University, Shanda SouthRoad #27, Jinan, Shandong, 250100, P. R. China, Jinan, 250100, China, (2) Chemistry Department, Shandong Academy of Medical Science, Jing 10 road, Jinan, Shandong, 250062, P. R. China, Jinan, China, (3) Chemistry College, Shandong University, Shanda SouthRoad #27, Jinan, 250100, China
Planar chirality keeps very important role in modern chemistry, in clued material to stereoselectivity organic chemistry. After first report ed in [2,2]paracyclophane chemistry study, this research field keeps interested till now. Recently, our research group and others' reported this series compounds shows great efficient in asymmetric catalysis. In order to de the further study in this field, large scale synthesis of pure chiral 4-amino-12-bromo[2,2]paracyclophane and 4,12-diamino[2,2]paracyclophane is necessary. Although there is few successful report in this filed by using Hartwig-Buchwald pathway, we make very important improvement by using co-catalyst B in the reaction. By adjusting the base loading, we could easily control for making mono- or dimmer-substuituent compounds.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006