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A Tailored Versatile and Efficient NHC‐Based NNC‐Pincer Manganese Catalyst for Hydrogenation of Polar Unsaturated Compounds

Zeyuan Wei, Hengxu Li, Yujie Wang, Qiang Liu

2023Angewandte Chemie International Edition70 citationsDOI

Abstract

The reactivity of metal-hydride complexes can be harnessed by the modification of ancillary ligands. With the aim of improving the hydride-donor ability of the key Mn-H intermediate and reducing steric hindrance, we herein report the rational design of a versatile and efficient NHC-based NNC-pincer Mn catalyst for hydrogenation reactions. This newly developed catalyst exhibited higher activity than the corresponding NNP-pincer Mn catalyst owing to its reduced steric hindrance and enhanced Mn-H σ-bonding orbital energy level through a π-antibonding interaction. Using this highly active NNC-pincer Mn catalyst, a rich array of polar unsaturated compounds (>80 examples) including esters, N-heteroarenes, amides, carbonates, and urea derivatives, were successfully hydrogenated under relatively mild conditions. This work represents a rare example of a general phosphine-free Mn-catalyzed hydrogenation system.

Topics & Concepts

Pincer movementSteric effectsCatalysisChemistryPhosphineReactivity (psychology)HydrideFrustrated Lewis pairCombinatorial chemistryManganesePhotochemistryOrganic chemistryMetalLewis acids and basesMedicinePathologyAlternative medicineAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisNanomaterials for catalytic reactions
A Tailored Versatile and Efficient NHC‐Based NNC‐Pincer Manganese Catalyst for Hydrogenation of Polar Unsaturated Compounds | Litcius