Moseen A. Shaikh, Sandip G. Agalave, A. S. Ubale
Jan 6, 2020
Citations
0
Influential Citations
11
Citations
Journal
The Journal of organic chemistry
Abstract
The sp3 C-H alkylation of 9H-fluorene using alcohol and Ru-catalyst via borrowing hydrogen concept has been described. This reaction was catalyzed by [Ru(p-cymene)Cl2]2 complex (3 mol%) and exhibited a broad reaction scope with different alcohols, allowing primary and secondary alcohols to be employed as non-hazardous and greener alkylating agents with the formation of environmentally benign water as a by-product. A variety of 9H-fluorene underwent selective and exclusive mono-C9-alkylation with primary alcohols in good to excellent isolated yield (26 examples, 50-92% yield). Whereas this reaction with secondary alcohols in the absence of any external oxidants furnished the tetrasubstituted alkene as major product. Further, a base mediated C-H hydroxylation of the synthesized 9H-fluorene derivatives afforded 9H-hydroxy functionalized quaternary fluorene derivatives in excellent yield.