Abstract Direct deoxygenative borylation is a highly enabling chemical transformation considering the attractive synthetic features of oxygenous feedstocks and organoboron compounds. Despite ranking among the synthetic ideality in different settings, such chemical space remained largely uncharted and underutilized until recent decades. This short review will summarize some key advances in the field of direct deoxy-borylation of alcohols, ethers, aldehydes, ketones, and carboxylic acids and organize these contributions based on substrate classes. In each representative, the general features, including reaction conditions, product scopes and mechanistic insights, will be highlighted and discussed.