In order to address this gap in the field, our lab recently described a catalytic process involving the reductive coupling of aliphatic aldehydes with alkyl bromides in a pathway proposed to proceed through the intermediacy of a-silyloxyalkylnickel intermediates derived from aldehydes, silyl chlorides, and low-valent nickel (Figure ). In order to address limitations of that protocol, including substrate access, scope, and yield, we have now explored the utility of more broadly available substrate classes in catalytic couplings with aliphatic aldehydes (Figure ). The main focus of this study is the coupling of aliphatic aldehydes with redox-active esters, providing access to numerous product types derived from simple carboxylic acid precursors. Additionally, preliminary examples of reductive couplings between aldehydes and alkyl tosylates or epoxides are described. This combination of procedures provides strategies where alkyl fragments are derived from carboxylic acids, alcohols, or alkenes, thus greatly expanding the range of precursors available for aldehyde functionalization processes. Our initial investigation geared towards developing the catalytic reductive coupling of aldehydes 1a with the N-hydroxyphthalimide (NHPI) ester 2a (Table ). Systematic investigation of the reaction parameters showed that the desired product 3a was isolated in good yield (91%) with a combination of Ni(cod)2 and bioxazoline (BiOx). Control experiments indicated that a nickel catalyst was necessary for the reaction to proceed, and other nickel sources only led to moderate yield (entries 2, 11 and 12). The ligand (BiOx), reductant (nanopower Zn), 1,5-hexadiene and LiCl also A. Grignard, Barbier, and Nozaki-Hiyama-Kishi couplings