Automated synthesis of complex biomolecules has had a major impact in the fields of chemistry, biochemistry, medicine, and healthcare. Indeed, the development of strategies based on iterative coupling of amino acid and nucleotide building blocks heralded the proteomic and genomic revolution. Substantial advancement has also been made towards automated polysaccharide synthesis. Iteration has been the cornerstone of all these successful automated synthesis technologies (Fig. ), with the building blocks being connected together by a single coupling reaction (e.g., amide, phosphonate, or glycosidic bond formation). In contrast, general, automated methodologies for C-C bond formation have not yet emerged due to the complexity and variety of organic molecules. However, some progress in automated organic synthesis has been achieved but only in the preparation of relatively simple targets; the field is still nascent. A notable example from Burke reported the iterative assembly of polyenes, where alkene building blocks were coupled together through Suzuki-Miyaura reactions of MIDA boronates. In this example, C(sp 2 )-C(sp 2 ) bonds were formed and a maximum of three iterations were described. Recently, the same group reported C(sp 3 )-C(sp 3 ) bond-forming reactions in an automated fashion but, again only a small number (two) of automated iterations were described. Over the last decade we have been interested in developing robust, iterative methodologies that have the potential to be automated. In particular, we have developed strategies based on boron homologations with chiral carbenoid building blocks which allow carbon chains to be grown one-atom-at-a-time with complete stereocontrol (Fig. ). In fact, our methodology was used by Burke for the automated coupling of different boron-containing building blocks to form C(sp 3 )-C(sp 3 ) bonds. We have demonstrated that boron homologations can be performed in an iterative fashion, in a process termed assembly-line synthesis. The advantages of this process include (i) it employs a single set of reaction conditions; (ii) it can be done iteratively without purification of intermediates; (iii) no additional manipulations are required between homologation steps (e.g., protection or redox steps); and (iv) it uses a small set of common repeat building blocks. These features make this chemistry uniquely suited for automation, since all other automated iterative synthesis technologies require additional deprotection steps between each coupling reaction. Whilst these boron homologation reactions are efficient when performed manually in the laboratory, the air-sensitive organometallic reagents and thermally unstable carbenoids require an inert atmosphere and low temperatures. These conditions are difficult to achieve in automated chemical synthesis since most platforms are not designed for use under such extreme environments. Herein, we describe a novel automated methodology that allows iterative and stereoselective C(sp 3 )-C(sp 3 ) bond formation (Fig. ). Successful handling of air-sensitive reactants at low temperatures allowed numerous iterations to be performed in a stereocontrolled fashion. Moreover, functionalization of the elongated carbon chain has also been developed, thus showing how a single robotic platform is capable of performing diverse chemical reactions.