An alternative approach for functionalization α to oxygen involves the generation and capture of α-oxy radical intermediates, which have been developed as highly useful cross-coupling partners using nickel catalysis. Among these approaches, ketyl radicals offer a versatile platform of reactivity for reversing the traditional electrophilic character of carbonyls and play a pivotal role in numerous bond-forming and bond-breaking processes including ketyl-olefin couplings. The requirement for strong, stoichiometric reductants, however, places practical limits on the synthetic utility of ketyl intermediates generated by classical approaches. Several innovative strategies to generate ketyl radical were recently reported through processes such as concerted proton-coupled electron transfer, Lewis acid-facilitated photocatalytic reduction, 18 redox-neutral photochemical promotion through transient a-acetoxy vinyl iodides intermediate, and electrocatalytic reduction. Recent efforts in our laboratory have identified the addition of Ni(0) to aliphatic aldehydes through the activation by silyl halides as an alternative strategy for promoting reductive cross couplings of aldehydes either involving cyclization of an ynal with alkylation by an alkyl bromide or through direct coupling of the aldehyde with alkyl electrophiles. By analogy, we envisioned that trifluoromethyl-substituted alkenes might serves as competent electrophiles in cross couplings with aldehydes under reductive conditions. This outcome would enable reactivity that serves as a functional synthetic equivalent of ketyl radicals through activation of the aldehyde by a low-valent nickel species in the presence of a silyl chloride. The 1,1-difluoroalkenes obtained through reductive couplings of aldehydes with trifluoromethyl-substituted alkenes with extrusion of a single fluorine atom are intriguing motifs owing to their presence in a number of biologically active compounds. Due to their resistance to in vivo metabolism, gem-difluoroalkenes are a promising carbonyl bioisostere owing to their steric and electronic similarity to aldehydes, ketones, and esters, offering new opportunities in the drug discovery pipeline. Commonly, gemdifluoroalkenes are typically prepared by synthetic routes involving gem-difluoroolefination of diazo or carbonyl precursors, highly reactive organometallic species or strong base-mediated nucleophilic addition to α-trifluoromethyl alkenes, suffering from the limited functional group tolerance and narrow substrates scope, due to the harsh reaction conditions. However, considerable progress has been made with expanded reaction scope in the field of photo-, or transition metalcaralyzed 27 redox-neutral allylic defluorinative cross-coupling reactions. Recently, Wang and other groups have established Ni-and Ti-catalyzed reductive defluorinative couplings between different electrophiles with trifluoromethyl alkenes to further expand the diversity of gemdifluoroalkenes, but approaches to gem-difluoroalkenes bearing additional functionality are still limited. Herein, we describe efficient nickel-catalyzed defluorinative couplings of trifluoromethyl-substituted alkenes with aliphatic aldehydes to provide homoallylic alcohols possessing the gemdifluoroalkenes structural motif. These advances further establish effective strategies for the nickel-catalyzed functionalization of simple aliphatic aldehydes, and the mechanistic findings presented highlight the impact of subtle modifications of the reactant structure and ligand motif employed.