The addition of alkyl fragments to aliphatic aldehydes {is a|is really a|is actually a|can be a|is often a|is usually a} {highly|extremely|very|hugely} desirable transformation for fragment couplings, {yet|however|but} {existing|current} {methods|techniques|strategies|approaches|procedures|solutions} {come with|include} operational challenges {related|associated|connected} {to the|towards the|for the} basicity and instability {of the|from the|in the|on the|with the|of your} nucleophilic reagents {commonly|generally|typically|frequently|normally|usually} employed. We report herein that nickel catalysis {using|utilizing|making use of|employing|working with|applying} a readily {available|accessible|obtainable|offered|readily available|out there} bioxazoline (BiOx) ligand can catalyze the reductive coupling of redox-active esters with aliphatic aldehydes {using|utilizing|making use of|employing|working with|applying} zinc metal {as the|because the} {reducing|decreasing|lowering|minimizing} agent to {deliver|provide} silyl-protected secondary alcohols. This protocol is operationally {simple|easy|straightforward|basic|uncomplicated|very simple}, proceeds {under|below|beneath} mild {conditions|circumstances|situations}, and tolerates {a variety of|a number of|many different|various|a range of|several different} functional groups. Initial mechanistic {studies|research} {suggest|recommend} a radical chain pathway. {Additionally|In addition|Furthermore|Moreover|Also|On top of that}, alkyl tosylates and epoxides are {suitable|appropriate} alkyl precursors to this transformation {providing|supplying|offering|delivering|giving} a versatile suite of catalytic reactions for the functionalization of aliphatic aldehydes. XantPhos Pd G3 uses 3-Chloropropionaldehydediethylacetal Chemscene PMID:24275718
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