Jian-min Fu, V. Snieckus
Jun 1, 2000
Citations
0
Influential Citations
37
Citations
Journal
Canadian Journal of Chemistry
Abstract
A new general and regiospecific synthesis of 9-phenanthrols (1 +2 3 4, Scheme 1, Table 1) proceeding by a Directed ortho Metalation (DoM), Suzuki-Miyaura cross coupling, and a new LDA-mediated Directed remote Metalation sequence is described. The facile Pd-catalyzed hydrogenolysis of the phenanthrols 4 into the corresponding phenanthrenes 5 via their triflates 18 translates the original DoM regioselectivity also into a general synthesis of phenanthrenes (Table 2). Further DoM (19 20, 21; 24 25), cross coupling (20c 23), as well as oxidation - ring contraction (4b, 4f 28a, 28b) chemistry of phenanthrene derivatives is reported.Key words: 9-phenanthrols, directed ortho metalation, Suzuki cross coupling, synthesis.