Stable and Easily Handled Fe<sup>III</sup> Catalysts for Hydrosilylation of Ketones and Aldehydes

Zhu, Kailong; Shaver, Michael P.; Thomas, Stephen P.

doi:10.1002/ejoc.201500090

Cited by 24 publications

(5 citation statements)

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“…However, the high catalyst loading (30 mol %) and reaction temperature (60 °C) diminish the overall reaction efficiency. Our success with amine‐bis(phenolate) iron(III) catalyzed hydrosilylation and mediation of radical reactions such as atom transfer radical polymerization suggested these could be ideal catalysts for this formal hydroamination process. In addition, the synthesis of amine‐bis(phenolate) iron(III) complexes is straightforward and they are highly stable towards air and moisture…”

Section: Methodsmentioning

confidence: 99%

“…The reaction showedg ood functional group tolerance including substrates bearinga na mide, ketone,h alide, and alcohol functionalities, showcasing this as ap otent tool for the construction of highly functionalized amines.E xcellentr egioselectivity for amination at the most substituted carbon centerw as observed for this radicalreaction, in contrast to transition-metal-catalyzed hydroamination reactions, in whichs trict control of regioselectivity remainsc hallenging. However, the high catalyst loading (30 mol %) and reactiont emperature (60 8C) diminish the overall reaction efficiency.O ur successw ith amine-bis(phenolate) iron(III) catalyzed hydrosilylation [7] and mediation of radicalr eactions such as atom transfer radical polymerization [8] suggested these could be ideal catalysts for this formal hydroamination process. In addition, the synthesis of amine-bis(phenolate) iron(III) complexes is straightforwarda nd they are highly stable towardsair and moisture.…”

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confidence: 99%

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Amine‐bis(phenolate) Iron(III)‐Catalyzed Formal Hydroamination of Olefins

Zhu

Shaver

Thomas

2016

Chemistry An Asian Journal

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Section: Methodsmentioning

confidence: 99%

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Amine‐bis(phenolate) Iron(III)‐Catalyzed Formal Hydroamination of Olefins

Zhu

Shaver

Thomas

2016

Chemistry An Asian Journal

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“…Thomas then showed that the amine−bis(phenolate) iron(III) (C177) (1.0 mol %) with (EtO) 3 SiH (3.0 equiv) at 80 °C for 3−24 h promoted the hydrosilylation of both ketones and aldehydes with wide functional group tolerance and 55−97% yields (Scheme 79). 338 Fernandez described iron complexes based on anthraquinonic ligands C178 339 and C179, 340 which were active in the hydrosilylation of aldehydes and ketones. More particularly, complex C179 (0.25−0.5 mol %) exhibited TOFs up to 63 min −1 when performing the reaction at room temperature for 5−120 min in the presence of 1.12 equiv of (EtO) 2 MeSiH.…”

Section: Aldehydes and Ketonesmentioning

confidence: 99%

Iron Catalysis in Reduction and Hydrometalation Reactions

2018

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The last two decades have seen an impressive improvement of the use of iron as a fascinating and valuable alternative transition metal in homogeneous catalysis in terms of sustainability and economy. It was efficiently used in catalytic organic synthetic transformations, which in particular include the reduction of unsaturated bonds. This review summarizes the fast development and the recent advances in selective reductions of olefins, alkynes, carbonyl and carboxylic derivatives, imines, and nitro compounds promoted by iron catalysts. The topical hydrogen-borrowing reactions and hydroboration of unsaturated compounds are also reported. It is hoped that this account not only provides an overview of the state of the art in iron catalysis but also stimulates the development of superior greener catalytic systems in the near future.

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“…One year later, following a seminal work on the chemoselective hydrosilylation of carbonyl derivatives, Thomas reported the same reaction using 2 mol‐% of the stable iron(III) catalyst 42 in the presence of 2 equiv. of (EtO) 3 SiH in ethanol at r.t. for 1–2 h (Scheme ) , .…”

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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Stable and Easily Handled Fe^III Catalysts for Hydrosilylation of Ketones and Aldehydes

Cited by 24 publications

References 46 publications

Amine‐bis(phenolate) Iron(III)‐Catalyzed Formal Hydroamination of Olefins

Amine‐bis(phenolate) Iron(III)‐Catalyzed Formal Hydroamination of Olefins

Iron Catalysis in Reduction and Hydrometalation Reactions

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

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Stable and Easily Handled FeIII Catalysts for Hydrosilylation of Ketones and Aldehydes

Cited by 24 publications

References 46 publications

Amine‐bis(phenolate) Iron(III)‐Catalyzed Formal Hydroamination of Olefins

Amine‐bis(phenolate) Iron(III)‐Catalyzed Formal Hydroamination of Olefins

Iron Catalysis in Reduction and Hydrometalation Reactions

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

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Stable and Easily Handled Fe^III Catalysts for Hydrosilylation of Ketones and Aldehydes