A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC–Fe(0) Complex

Bhunia, Mrinal; Hota, Pradip Kumar; Vijaykumar, Gonela; Adhikari, Debashis; Mandal, Swadhin K.

doi:10.1021/acs.organomet.6b00478

Cited by 52 publications

(36 citation statements)

References 83 publications

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“…Catalyst‐free hydroboration of ketimines is expected to be difficult as compared to analogues aldimines due to less electrophilicity coupled with more steric congestion around the imine moiety. After having success with aldimines, we focused on the hydroboration of ketimines using our catalyst‐free and solvent‐free approach.…”

Section: Methodsmentioning

confidence: 99%

Catalyst‐Free and Solvent‐Free Facile Hydroboration of Imines

Pandey

Donthireddy

Rit

2019

Chemistry An Asian Journal

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A facile process for the catalyst‐free and solvent‐free hydroboration of aromatic as well as heteroaromatic imines is reported. This atom‐economic methodology is scalable, compatible with sterically and electronically diverse imines, displaying excellent tolerance towards various functional groups, and works efficiently at ambient temperature in most of the cases, affording secondary amines in good to excellent yield after hydrolysis.

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Section: Methodsmentioning

confidence: 99%

Catalyst‐Free and Solvent‐Free Facile Hydroboration of Imines

Pandey

Donthireddy

Rit

2019

Chemistry An Asian Journal

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“…In a mechanism point of view, based on the previous reaction pathway proposed with indium, [8] an imine intermediate C could be firstly generated from the condensation of LA with amine and dehydrogenative silylation of carboxylic acid with hydrosilanes. (Scheme 2) Then the imine moiety of C was reduced under catalytic hydrosilylation conditions leading to silylamine species D [20,24] which underwent transamidation generating 4a. Finally, 4a could be further reduced into 3a under catalytic hydrosilylation conditions.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Iron‐Catalysed Switchable Synthesis of Pyrrolidines vs Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives via Hydrosilylation

2019

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A selective production of pyrrolidines vs pyrrolidinones via hydrosilylation of levulinic acid and levulinates by switching of the iron complex catalyst is presented herein. The reactions proceeded efficiently with various anilines and alkylamines under both visible light irradiation and thermal conditions with 43 examples in isolated yields up to 93%. Noticeably, under similar conditions, cyclic amines such as piperidines and azepanes were efficiently synthesized with yields up to 92%, by reaction of anilines with 1,5-or 1,6-keto acids, respectively. Similarly, N-arylinsolidoline compounds can be prepared from 2-formylbenzoic acid in 57-93% yields.

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“…In 2016, Mandal described a highly efficient catalytic system for the reduction of imines to amines using the related abnormal a NHC−Fe(0) complex 17 depicted in (Scheme ) . Abnormal N‐heterocyclic carbenes, which were pioneered by Crabtree and Bertrand, are proved to be better σ‐donors than classical NHCs.…”

Section: Hydrosilylationmentioning

confidence: 99%

“…In fact, comparing the catalytic efficiency of 17 with 16 bearing a classical NHC in the hydrosilylation of imines, it was observed the better performance of complex 17 . The stronger donating a NHC ligand makes the iron(0) center more electron rich, facilitating the oxidative addition of silane …”

Section: Hydrosilylationmentioning

confidence: 99%

Iron N‐Heterocyclic Carbenes in Reduction Reactions

Lopes

Royo

2017

Israel Journal of Chemistry

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Iron N-heterocyclic carbene research has witnessed a spectacular growth in the last decade. A wide number of catalytic applications have been recently disclosed, demonstrating the enormous potential of Fe-NHCs in organic synthesis. Catalytic reductions of multiple bonds through hydrogenation, transfer hydrogenation, hydrosilylation and hydroboration processes constitute important transforma-tions. To date, this field of research is still in its infancy. Over the past few years our group has contributed to this area by developing new efficient and selective iron-NHC complexes for the reduction of unsaturated organic groups. This review provides a concise overview of Fe-NHC catalysed reduction reactions to push for further progress in this exciting area of research.

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A Highly Efficient Base-Metal Catalyst: Chemoselective Reduction of Imines to Amines Using An Abnormal-NHC–Fe(0) Complex

Abstract: VII. Optimisation study for the reduction of4-methyl-N-(1-phenylethylidene)aniline....S14 VIII. General procedure for catalytic hydrosilylation of ketimines to secondary amines and characterization data.

Cited by 52 publications

References 83 publications

Catalyst‐Free and Solvent‐Free Facile Hydroboration of Imines

Catalyst‐Free and Solvent‐Free Facile Hydroboration of Imines

Iron‐Catalysed Switchable Synthesis of Pyrrolidines vs Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives via Hydrosilylation

Iron N‐Heterocyclic Carbenes in Reduction Reactions

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