Reactions of Aldehydes and Ketones and their Derivatives

A photocatalytic traceless C–N bond formation/cleavage strategy enabling the use of (α-chiral) alkyl aldehydes as deoxygenative (chiral) alkyl radical equivalents

“…2 c – f ,3,6 In this regard, alkyl aldehydes are ideal alkyl radical precursors due to their advantages of abundant natural stock, convenient preparation, easy commercialization and relatively low toxicity. 7 The typical strategy for the utilization of alkyl aldehydes as alkyl radical equivalents is via decarbonylation reactions (Scheme 1a). 7 b , c Despite the usefulness of this strategy in alkylation reactions, it has several intrinsic limitations that are hard to overcome: (1) the coexisting nucleophilic acyl radicals will compete and interfere with the alkyl radicals to trigger undesired side reactions; 8 (2) the decarbonylation processes will inevitably change the carbon-skeleton of the related alkyl radical species in comparison with their source mother aldehydes; 7 b , c and (3) it will be particularly disadvantageous when α-chiral alkyl aldehydes are used for the generation of alkyl radical species because decarbonylation processes will lead to the elimination of the original α-chiral centers of the mother aldehydes.…”