Asymmetric Transfer and Pressure Hydrogenation with Earth‐Abundant Transition Metal Catalysts

Zhang, Zhenfeng; Butt, Nicholas; Zhou, Muxing; Liu, Delong; Zhang, Wanbin

doi:10.1002/cjoc.201800053

Cited by 158 publications

(46 citation statements)

References 94 publications

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“…1 a) 1 – 15 . Over the past half-century, significant progress has been made in the catalytic asymmetric hydrogenation of various imines for the synthesis of chiral amines 16 – 23 . Imines bearing relatively small substituents, such as methyl or ethyl groups directly connected to the carbon atom of a C = N group, have been widely used as substrates in asymmetric hydrogenation for the preparation of chiral amines, providing excellent stereoselectivities 16 – 27 .…”

Section: Introductionmentioning

confidence: 99%

Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Chen

Zhang

et al. 2018

Nat Commun

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Asymmetric hydrogenation of sterically hindered substrates still constitutes a long-standing challenge in the area of asymmetric catalysis. Herein, an efficient palladium acetate (an inexpensive Pd salt with low toxicity) catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines is realized with high catalytic activities (S/C up to 5000) and excellent enantioselectivities (ee up to 99.9%). Quantum chemical calculations suggest that uniformly high enantioselectivities are observed due to the structurally different S- and R-reaction pathways.

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Section: Introductionmentioning

confidence: 99%

Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Chen

Zhang

et al. 2018

Nat Commun

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“…[1] In contrast, chiral catalysts made of earthabundant metals, [2] fore xample,c opper, [3] nickel, [4] iron, [5] or cobalt, [6] have only gained some recent popularity in this area. [1] In contrast, chiral catalysts made of earthabundant metals, [2] fore xample,c opper, [3] nickel, [4] iron, [5] or cobalt, [6] have only gained some recent popularity in this area.…”

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confidence: 99%

Lutidine‐Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones

et al. 2019

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Aseries of Mn I complexes containing lutidine-based chiral pincer ligands with modular and tunable structures has been developed. The complex shows unprecedentedly high activities (up to 9800 TON; TON = turnover number), broad substrate scope (81 examples), good functional-group tolerance,a nd excellent enantioselectivities (85-98 %e e) in the hydrogenation of various ketones.T hese aspects are rare in earth-abundant metal catalyzedhydrogenations.T he utility of the protocol have been demonstrated in the asymmetric synthesis of av ariety of key intermediates for chiral drugs. Preliminary mechanistic investigations indicate that an outersphere mode of substrate-catalyst interactions probably dominates the catalysis.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…For this purpose, iron is one of the most abundant transition metals in the Earth's crust, making it one tremendously attractive candidate for catalytic applications due to its low price and toxicity. Thus, since two decades, its use in catalysed transformations has seen an impressive increase, more particularly in the reduction area …”

Section: Introductionmentioning

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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Asymmetric Transfer and Pressure Hydrogenation with Earth‐Abundant Transition Metal Catalysts

Cited by 158 publications

References 94 publications

Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Pd(OAc)2-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Lutidine‐Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones

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

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