Synthesis of Ru(II) complexes containing N-heterocyclic carbenes functionalized with secondary donor groups: Catalytic activity toward enantioselective transfer hydrogenation

Yoshimura, Misato; Kamisue, Ryo; Sakaguchi, Satoshi

doi:10.1016/j.jorganchem.2013.04.028

Cited by 31 publications

(10 citation statements)

References 66 publications

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“…A different approach for the improvement of chiral ruthenium (II) NHC catalysts was conducted by Sakaguchi et al, who described a series of chiral NHCs with different arene backbones (Fig. 19) [105].…”

Section: Table 13mentioning

confidence: 99%

Current advances on ruthenium(II) N-heterocyclic carbenes in hydrogenation reactions

Hey

Reich

Baratta

et al. 2018

Coordination Chemistry Reviews

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This review provides a brief overview of advances on ruthenium(II) N-heterocyclic carbene complexes 30 (NHCs) applied for hydrogenation reactions undertaken during the last five years. Several structural 31 motifs, containing mono-, bi-, tri-and tetradentate binding modes of the NHCs are discussed in combi-32 nation with a variety of different wingtip substituents to provide active catalysts for hydrogenation reac-33 tions. While bidentate ligands are the more active catalysts than their monodentate analogues, pincer 34 ligands must be chosen carefully to enable the formation of a free coordination site in catalysis. 35 Transfer hydrogenation and direct hydrogenation of ketones and aldehydes, olefins, nitriles, imines 36 and esters are summarized, showing the trend towards hydrogen transfer from other sources than hydro-37 gen gas. Recently developed chiral NHCs offer the opportunity for asymmetric transformations as a pos-38 sible pathway to access natural products.

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Section: Table 13mentioning

confidence: 99%

Current advances on ruthenium(II) N-heterocyclic carbenes in hydrogenation reactions

Hey

Reich

Baratta

et al. 2018

Coordination Chemistry Reviews

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“…There are several review articles reported in the past decade, which are dedicated to NHC ligands bearing one additional donor group [ 7 , 8 , 9 , 10 ]. Included in these review articles are bidentate NHC ligands with phosphorous tether [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ], nitrogen [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ], and oxygen tethers [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 ,…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Catalysis Involving Bidentate N-Heterocyclic Carbene Ligands

2021

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Since the discovery of persistent carbenes by the isolation of 1,3-di-l-adamantylimidazol-2-ylidene by Arduengo and coworkers, we witnessed a fast growth in the design and applications of this class of ligands and their metal complexes. Modular synthesis and ease of electronic and steric adjustability made this class of sigma donors highly popular among chemists. While the nature of the metal-carbon bond in transition metal complexes bearing N-heterocyclic carbenes (NHCs) is predominantly considered to be neutral sigma or dative bonds, the strength of the bond is highly dependent on the energy match between the highest occupied molecular orbital (HOMO) of the NHC ligand and that of the metal ion. Because of their versatility, the coordination chemistry of NHC ligands with was explored with almost all transition metal ions. Other than the transition metals, NHCs are also capable of establishing a chemical bond with the main group elements. The advances in the catalytic applications of the NHC ligands linked with a second tether are discussed. For clarity, more frequently targeted catalytic reactions are considered first. Carbon–carbon coupling reactions, transfer hydrogenation of alkenes and carbonyl compounds, ketone hydrosilylation, and chiral catalysis are among highly popular reactions. Areas where the efficacy of the NHC based catalytic systems were explored to a lesser extent include CO2 reduction, C-H borylation, alkyl amination, and hydroamination reactions. Furthermore, the synthesis and applications of transition metal complexes are covered.

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“…In this scenario, the catalytic hydrogenation of ketones in both achiral and chiral fashions has recently gained prominence . Interestingly, though the transition‐metal complexes of N‐heterocyclic carbenes have been studied extensively for the transfer hydrogenation of ketones to alcohols,, reports of the related chiral versions are surprisingly few …”

Section: Introductionmentioning

confidence: 99%

Chiral Oxazolidine‐Fused N‐Heterocyclic Carbene Complexes of Rhodium and Iridium and Their Utility in the Asymmetric Transfer Hydrogenation of Ketones

2017

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The catalytic potential of new N-heterocyclic carbene ligands, derived from a chiral fused bicyclic ring scaffold with restricted rotation along the C-N bond bearing the chiral auxiliary, has been explored in the transition-metal-mediated asymmetric transfer hydrogenation reactions of ketones. In particular, the chiral oxazolidine-fused N-heterocyclic carbene precursors (3S)-3-R-6-methyl-7-phenyl-2,3-dihydroimidazo[5,1-b]oxazol-6-ium iodide [R = sec-butyl (1f ), i-butyl (2f ), isopropyl (3f )] were synthesized from commercially available optically pure amino acids in a multistep sequence that avoids tedious chiral resolution. The reactions of the chiral imidazolium iodide salts 1f-3f with Ag 2 O yielded the corresponding silver complexes [a]

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Synthesis of Ru(II) complexes containing N-heterocyclic carbenes functionalized with secondary donor groups: Catalytic activity toward enantioselective transfer hydrogenation

Cited by 31 publications

References 66 publications

Current advances on ruthenium(II) N-heterocyclic carbenes in hydrogenation reactions

Current advances on ruthenium(II) N-heterocyclic carbenes in hydrogenation reactions

Recent Advances in Catalysis Involving Bidentate N-Heterocyclic Carbene Ligands

Chiral Oxazolidine‐Fused N‐Heterocyclic Carbene Complexes of Rhodium and Iridium and Their Utility in the Asymmetric Transfer Hydrogenation of Ketones

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