Enantioselective hydrosilylation of unsaturated carbon-heteroatom bonds (C&z.dbd;N, C&z.dbd;O) catalyzed by [Ru-S] complexes: a theoretical study

A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst [Ru-S] ([ L* -Ru(SDmp)] + [BAr 4 F ] − ) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways l...

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Published inRSC advances Vol. 1; no. 16; pp. 9431 - 9437
Main Authors Zhou, Miao-Miao, Chen, Guanghui, Dang, Li
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 04.03.2020
The Royal Society of Chemistry
Subjects
Carbon
Cartesian coordinates
catalysts
Cations
Chemistry
chemoselectivity
cleavage (chemistry)
Dehydrogenation
Density functional theory
enamines
Enantiomers
enantioselectivity
enol ethers
hydrogen
Hydrogen bonds
Hydrosilylation
Imines
Ketones
Lewis acids
Ligands
phosphine
Phosphines
Reaction mechanisms
Ruthenium
Ruthenium compounds
silane
Silicon
silylation
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Abstract A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst [Ru-S] ([ L* -Ru(SDmp)] + [BAr 4 F ] − ) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru-S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si-H bond cleavage by the dual activity of Ru-S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to N&z.dbd;C/O&z.dbd;C; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to N&z.dbd;C/O&z.dbd;C is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods. A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst with a chiral monodentate phosphine ligand is carried out in this work.
AbstractList A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium(ii) thiolate catalyst [Ru-S] ([L*-Ru(SDmp)] [BAr ] ) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru-S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si-H bond cleavage by the dual activity of Ru-S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to N[double bond, length as m-dash]C/O[double bond, length as m-dash]C; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to N[double bond, length as m-dash]C/O[double bond, length as m-dash]C is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods.
A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst [Ru-S] ([ L* -Ru(SDmp)] + [BAr 4 F ] − ) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru-S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si-H bond cleavage by the dual activity of Ru-S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to N&z.dbd;C/O&z.dbd;C; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to N&z.dbd;C/O&z.dbd;C is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods. A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst with a chiral monodentate phosphine ligand is carried out in this work.
A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium(ii) thiolate catalyst [Ru–S] ([L*-Ru(SDmp)]⁺[BAr₄F]⁻) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru–S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si–H bond cleavage by the dual activity of Ru–S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to NC/OC; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to NC/OC is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods.
A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst [Ru–S] ([L*-Ru(SDmp)] + [BAr 4 F ] − ) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru–S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si–H bond cleavage by the dual activity of Ru–S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to N C/O C; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to N C/O C is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods. A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst with a chiral monodentate phosphine ligand is carried out in this work.
A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst [Ru–S] ([ L* -Ru(SDmp)] + [BAr 4 F ] − ) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru–S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si–H bond cleavage by the dual activity of Ru–S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to NC/OC; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to NC/OC is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods.
A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium(ii) thiolate catalyst [Ru–S] ([L*-Ru(SDmp)]+[BAr4F]−) with a chiral monodentate phosphine ligand is carried out in this work. We elucidate all the pathways leading to the main products or by products mediated by the [Ru–S] complex in order to have deep understanding of the chemoselectivity and enantioselectivity. The DFT (Density Functional Theory) calculations show that the reaction mechanism including: (1) Si–H bond cleavage by the dual activity of Ru–S bond; (2) the generation of a sulfur-stabilized silane cation; (3) the electrophilic attack of silane cation to N=C/O=C; (4) hydrogen transfer from Ru to carbon cation. The hydrosilylation products are found to be the final products rather than the dehydrogenative ones, which is consistent with the experimental results. The dehydrogenative silylation reaction pathways which give N- or O-silylated enamine/enol ether are reversible according to our calculations. The computational results also show that the electrophilic attack of silicon to N=C/O=C is the rate-determining step and the ee value can be improved significantly with more bulky model phosphine ligand based on the same calculation methods.
Author Zhou, Miao-Miao
Chen, Guanghui
Dang, Li
AuthorAffiliation Department of Chemistry
Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province
Shantou University
AuthorAffiliation_xml – name: Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province
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  surname: Dang
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/35497244$$D View this record in MEDLINE/PubMed
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Electronic supplementary information (ESI) available: Details of computational methods, alternative energy profiles, tables of calculated energies and computed cartesian coordinates, full
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Snippet A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium( ii ) thiolate catalyst...
A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium(ii) thiolate catalyst...
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SubjectTerms Carbon
Cartesian coordinates
catalysts
Cations
Chemistry
chemoselectivity
cleavage (chemistry)
Dehydrogenation
Density functional theory
enamines
Enantiomers
enantioselectivity
enol ethers
hydrogen
Hydrogen bonds
Hydrosilylation
Imines
Ketones
Lewis acids
Ligands
phosphine
Phosphines
Reaction mechanisms
Ruthenium
Ruthenium compounds
silane
Silicon
silylation
Title Enantioselective hydrosilylation of unsaturated carbon-heteroatom bonds (C&z.dbd;N, C&z.dbd;O) catalyzed by [Ru-S] complexes: a theoretical study
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