Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system

Pehlivan, Leyla; Métay, Estelle; Laval, S.; Dayoub, Wissam; Demonchaux, Patrice; Mignani, Gérard; Lemaire, Marc

doi:10.1016/j.tet.2010.12.070

Cited by 77 publications

(32 citation statements)

References 31 publications

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“…Although Fe(acac)3 12 and ReIO2(PPh3)2 10 have been proved as effective catalysts, the chemoselectivity of carbonyl group did not realize. To our surprise, herein, we found the atalytic system from Ni(acac)2 and PMHS is a more efficient catalysts with high chemoselectivity of several kinds of functional groups besides carbonyl group (Scheme 2, 2r).…”

Section: Scheme 1 Different Processes For the Reduction Of Nitro-commentioning

confidence: 99%

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Selective reduction of nitro-compounds to primary amines by nickel-catalyzed hydrosilylative reduction

Sun

Quan

2015

RSC Adv.

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Section: Scheme 1 Different Processes For the Reduction Of Nitro-commentioning

confidence: 99%

“…Although iron is a good alternative to noble metals, the chemoselectivity was not very good, and the tedious reaction time (24-48 h) was hard to accept. 12 Herein, we reported a convenient and efficient reduction of nitro-compounds with PMHS. After the exploratory study on the choice of the metal catalysts, nickel emerged as an ideal candidate.…”

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confidence: 99%

Selective reduction of nitro-compounds to primary amines by nickel-catalyzed hydrosilylative reduction

Sun

Quan

2015

RSC Adv.

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“…In the similar context, Lemaire and his group developed an efficient catalytic system for the reduction of nitroaromatics using the catalytic amount of Fe(acac) 3 and TMDS as hydride donor in THF at 60 °C (Scheme ) …”

Section: Hydrosilylation Of Nitroarenesmentioning

confidence: 99%

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Shaikh¹

2019

ChemistrySelect

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Iron catalyzed organic synthesis has emerged as a sustainable chemistry due to the highly competitive cost, high natural abundance and ecologically acceptable properties of iron. Moreover, its extensive range of oxidation states i. e. -II to + VI provides numerous opportunities to perform multiple organic reactions. Recently iron catalysis has started competing the established precious metals. Among organic scaffolds, amines are important building blocks that are useful in the various fields starting from drugs, crop protection chemicals to dyes and pigments. Typically, hydrogenation or reduction of functional groups such as imines, amides, nitroarenes and nitriles results into amines. In this context, homogeneous iron catalyzed hydrosilylation is a highly promising alternative to traditional hydrogenation and other reduction reactions. This review is focused on the synthesis of amine and its derivatives via hydrosilylation of imines, amides, nitroarenes and nitriles using iron as a catalyst. Some of the reduction methods of these functional groups that may not follow the typical hydrosilylation pathway are also included in this review due to their strong relevance to the theme. The phenomenal progress in this focused area is summarized to witness this transformation towards sustainable development in the field of amine synthesis.

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“…The reduction of nitroarenes is an important pathway to produce primary anilines and such transformations can be notably performed via iron‐catalysed reduction,, and notably hydrosilylation . Additionally, the hydroamination of olefins can be also performed with iron catalysts , .…”

Section: Multi‐step Reactions Involving Iron‐catalysed Hydrosilylamentioning

confidence: 99%

Multi‐Step Reactions Involving Iron‐Catalysed Reduction and Hydrogen Borrowing Reactions

2019

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Iron catalysis has seen an impressive breakthrough during the last two decades, and iron can now be considered as a valuable alternative transition metal for organic synthetic transformations. More precisely, in the reduction area, it became an efficient player for the selective reduction of olefins, alkynes, carbonyl and carboxylic derivatives, imines and nitro [a] Sortais. His work focuses on the homogeneous iron, manganese and rhenium-catalysed reduction and dehydrogenation reactions. Chakkrit Netkaew (left) was born in Nakhon Sawan, Thailand, in 1992. He completed his Bachelor's degree in Chemistry in 2017 from Mahidol University in Bangkok, Thailand, under the supervision of Assoc. Prof. Pasit Pakawatpanurut. After his graduation, he received a Franco-Thai scholarship 2018 from the French Embassy to attend the International Master's Program (Catalysis, Molecules and Green Chemistry) at the University of Rennes 1. Currently, he is carrying out research on the homogeneous iron-catalysed reduction reactions in Prof. C. Darcel's team. Prof. Christophe Darcel (centre) grew up in the north coast of Britany and studied chemistry at the University of Rennes 1, where he obtained his PhD in 1995 under the joint-supervision of Dr. Christian Bruneau and Prof. Pierre H. Dixneuf on Ru-and Pd-catalysed transformations of functional alkynes. After a year's postdoctoral stay with Prof. Wolfgang Oppolzer (Switzerland) working on sultam stereoselective chemistry and application in natural products synthesis, he then joined the group of Prof. Paul Knochel in Marburg (Germany) as an Alexander von Humboldt postdoctoral fellow and worked on the development of chiral zinc derivatives. In 1997, he was then appointed at the University of Cergy-Pontoise as assistant professor, and at the University of Burgundy as associate professor developing in collaboration with Prof. Sylvain Jugé P-chirogenic ligands for asymmetric catalysis. In 2007, he became full professor at the University of Rennes 1. His current research interests concentrate on homogeneous catalysis with particular emphasis on well-defined iron complexes in catalysis. 2474Scheme 12. Proposed mechanism for the selective formation of the secondary imines.Scheme 13. Selective reductive cross-coupling of nitriles and amines to form secondary aldimines. 2475Scheme 49. Iridium-iron-catalysed tandem conversion of alkanes to alkylsilanes. 2485 the use of CO 2 as a C1 building block, (ii) a step devoted to reduction of carboxylic derivatives, (iii) an enantioselective reduction step, and (iv) the use of biomass derivatives as starting materials.These achievements in iron-catalysed multi-step processes have already led to very impressive and promising results and will without any doubt stimulate their development in the near future.

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Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system

Cited by 77 publications

References 31 publications

Selective reduction of nitro-compounds to primary amines by nickel-catalyzed hydrosilylative reduction

Selective reduction of nitro-compounds to primary amines by nickel-catalyzed hydrosilylative reduction

Sustainable Amine Synthesis: Iron Catalyzed Reactions of Hydrosilanes with Imines, Amides, Nitroarenes and Nitriles

Multi‐Step Reactions Involving Iron‐Catalysed Reduction and Hydrogen Borrowing Reactions

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