Homologation reactions of organoboron compounds with carbenoid building blocks have been optimized and performed in an automated fashion on a commercially available robotic platform. These reactions, which require low temperature and water-and oxygen-free conditions, enable carbon chains to be grown one-atom-at-a-time with control of chain length and stereochemistry. Six iterative homologations were conducted by a non-synthesis expert, thus establishing the highest number of iterations reported for an automated synthesis of carbon chains. Finally, in addition to iterative homologations, we also demonstrated the automated conversion of boronic esters into amines, subsequent amide formation and alkylation, thereby significantly broadening the scope of reactions available. Since amines are ubiquitous in natural products and drug discovery, there is considerable potential of our automated synthesis for the preparation of complex molecules, even by non-experts.