Simple base-free Miyaura-type borylation of triarylantimony diacetates with tetra(alkoxo)diborons under aerobic conditions

•Miyaura-type borylation under aerobic conditions without any base was developed.•Triarylantimony diacetates can be used as new effective B-arylating agents.•A wide range of triarylantimony diacetates gave arylboronates with good to excellent yields.

The reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)2 (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free conditions. In the present reaction, two of the three aryl groups of antimony reagent were transferred to the coupling products when the reaction was carried out under aerobic conditions, although only one of the three aryl group of the antimony reagent was involved under an argon atmosphere. The broad scope of the reaction was demonstrated by using a variety of triarylantimony diacetates with sterically hindered aryl groups and highly reactive p-bromo-functionalized aryl derivatives.

Graphical abstractThe reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)2 (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free and aerobic conditions.Figure optionsDownload full-size imageDownload as PowerPoint slide