292863-15-1Relevant academic research and scientific papers
The directed ortho metalation - Palladium catalyzed cross coupling connection. A general regiospecific route to 9-phenanthrols and phenanthrenes. Exploratory further metalation
Fu, Jian-Min,Snieckus, Victor
, p. 905 - 919 (2007/10/03)
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 crocs 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.
