Metal-free Borylation of α-Naphthamides and Phenylacetic Acid Drug.

Abstract

Site-selective C-H borylation is an important strategy for constructing molecular diversity in arenes and heteroarenes. Although transition-metal-catalyzed borylation is well explored, developing metal-free strategies remains scarce. Herein, we developed a straightforward approach for BBr3-mediated selective C-H borylation of naphthamide and phenyl acetamide derivatives under metal-free conditions. This methodology appears to be economical and cost-effective. Successful borylation of drug molecules such as ibuprofen and indoprofen demonstrates the versatility and utility of this metal-free borylation. An exclusive monoselectivity was observed without a trace of diboration. Despite the possibility of forming a 5-membered boronated intermediate at the ortho-position, the selectively 6-membered intermediate paved the way for the formation of the peri-product, which was further supported by detailed computational investigation.