We report iridium-catalyzed C-H borylations for the regioselective synthesis of distally disubstituted calix4arene macrocycles. The atom- and step-economical method led to a broad family of calix4arenes in good yields and functional group tolerance. The synthetic utility of the C-H borylation protocol was finally illustrated with several late-stage modifications for the synthesis of elaborate calix4arenes frameworks, otherwise challenging to achieve with commonly employed procedures.We report iridium-catalyzed C-H borylations for the regioselective synthesis of distally disubstituted calix4arene macrocycles. The atom- and step-economical method led to a broad family of calix4arenes in good yields and functional group tolerance. The synthetic utility of the C-H borylation protocol was finally illustrated with several late-stage modifications for the synthesis of elaborate calix4arenes frameworks, otherwise challenging to achieve with commonly employed procedures.