Litcius/Paper detail

Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of <scp><i>N</i>‐Heterocycles</scp> via <scp>Manganese‐Catalyzed</scp> Dehydrogenative Cyclization

Zhihui Shao, Shanshan Yuan, Yibiao Li, Qiang Liu

2022Chinese Journal of Chemistry35 citationsDOI

Abstract

Comprehensive Summary The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese‐catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile synthesis of N ‐heterocycles. The in situ generated formaldehyde via catalytic methanol dehydrogenation can be selectively trapped by diverse dinucleophiles to avoid several possible side reactions. The utility of this transformation is further highlighted by its successful application to the synthesis of 13 C‐labeled N ‐heterocycles using 13 CH 3 OH as a readily accessible 13 C‐isotope reagent.

Topics & Concepts

ChemistryFormaldehydeMethanolCatalysisDehydrogenationManganeseReagentCombinatorial chemistryTransformation (genetics)Organic chemistryBiochemistryGeneAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisChemical Reactions and Isotopes