Competing dehalogenation versus borylation of aryl iodides and bromides under transition-metal-free basic conditions

Article abstract of DOI:10.1021/acs.joc.9b01350

In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as a hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the ^tBuOK/1,10-Phen-triggered radical nature of both competitive reactions has been revealed.