The Experts below are selected from a list of 1989 Experts worldwide ranked by ideXlab platform
Yasutaka Ishii - One of the best experts on this subject based on the ideXlab platform.
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Catalytic Reductive Alkylation of Secondary Amine with Aldehyde and Silane by an Iridium Compound
The Journal of organic chemistry, 2005Co-Authors: Tomoya Mizuta, And Satoshi Sakaguchi, Yasutaka IshiiAbstract:An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an Iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75 °C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of Iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an Iridium catalyst to afford the corresponding tertiary amines in good to excellent y...
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catalytic reductive alkylation of secondary amine with aldehyde and silane by an Iridium Compound
Journal of Organic Chemistry, 2005Co-Authors: Tomoya Mizuta, And Satoshi Sakaguchi, Yasutaka IshiiAbstract:An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an Iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75 °C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of Iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an Iridium catalyst to afford the corresponding tertiary amines in good to excellent y...
Nigam P. Rath - One of the best experts on this subject based on the ideXlab platform.
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Synthesis, Spectroscopy, Structure, and Reactivity of Azapentadienyl-Rhodium-Phosphine and Azapentadienyl-Iridium-Phosphine Complexes1
Organometallics, 2013Co-Authors: John R. Bleeke, Wipark Anutrasakda, Nigam P. RathAbstract:We report the synthesis, spectroscopy, structure, and reactivity of (1,2,3-η3)-(5-tert-butylazapentadienyl)Rh(PMe3)x (1, x = 2; 4, x = 3) and (1,2,3-η3)-(5-tert-butylazapentadienyl)Ir(PEt3)x (7, x = 2; 12, x = 3), which are produced by reacting [(cyclooctene)2M(μ-Cl)]2 with the appropriate amount of phosphine, followed by potassium tert-butylazapentadienide. Each of these Compounds reacts with 1 equivalent of triflic acid to produce a monoprotonation product. Rhodium Compounds 1 and 4 react at nitrogen to produce 2 and 5, respectively. Iridium Compound 7 reacts at the metal center, generating an Iridium-hydride product, 8, in which the azapentadienyl ligand coordinates in an unusual η3, η1-fashion, while Compound 12 reacts at nitrogen to produce 13. The monoprotonation products have been treated with additional acid, and in each case the secondary site of electrophilic addition has been determined. Rhodium Compounds 2 and 5 both react with a second equivalent of triflic acid at the metal center to produce...
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Synthesis, Spectroscopy, Structure, and Reactivity of Azapentadienyl-Rhodium-Phosphine and Azapentadienyl-Iridium-Phosphine Complexes1
Organometallics, 2013Co-Authors: John R. Bleeke, Wipark Anutrasakda, Nigam P. RathAbstract:We report the synthesis, spectroscopy, structure, and reactivity of (1,2,3-η3)-(5-tert-butylazapentadienyl)Rh(PMe3)x (1, x = 2; 4, x = 3) and (1,2,3-η3)-(5-tert-butylazapentadienyl)Ir(PEt3)x (7, x = 2; 12, x = 3), which are produced by reacting [(cyclooctene)2M(μ-Cl)]2 with the appropriate amount of phosphine, followed by potassium tert-butylazapentadienide. Each of these Compounds reacts with 1 equivalent of triflic acid to produce a monoprotonation product. Rhodium Compounds 1 and 4 react at nitrogen to produce 2 and 5, respectively. Iridium Compound 7 reacts at the metal center, generating an Iridium-hydride product, 8, in which the azapentadienyl ligand coordinates in an unusual η3, η1-fashion, while Compound 12 reacts at nitrogen to produce 13. The monoprotonation products have been treated with additional acid, and in each case the secondary site of electrophilic addition has been determined. Rhodium Compounds 2 and 5 both react with a second equivalent of triflic acid at the metal center to produce...
Tomoya Mizuta - One of the best experts on this subject based on the ideXlab platform.
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Catalytic Reductive Alkylation of Secondary Amine with Aldehyde and Silane by an Iridium Compound
The Journal of organic chemistry, 2005Co-Authors: Tomoya Mizuta, And Satoshi Sakaguchi, Yasutaka IshiiAbstract:An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an Iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75 °C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of Iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an Iridium catalyst to afford the corresponding tertiary amines in good to excellent y...
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catalytic reductive alkylation of secondary amine with aldehyde and silane by an Iridium Compound
Journal of Organic Chemistry, 2005Co-Authors: Tomoya Mizuta, And Satoshi Sakaguchi, Yasutaka IshiiAbstract:An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an Iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75 °C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of Iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an Iridium catalyst to afford the corresponding tertiary amines in good to excellent y...
John R. Bleeke - One of the best experts on this subject based on the ideXlab platform.
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Synthesis, Spectroscopy, Structure, and Reactivity of Azapentadienyl-Rhodium-Phosphine and Azapentadienyl-Iridium-Phosphine Complexes1
Organometallics, 2013Co-Authors: John R. Bleeke, Wipark Anutrasakda, Nigam P. RathAbstract:We report the synthesis, spectroscopy, structure, and reactivity of (1,2,3-η3)-(5-tert-butylazapentadienyl)Rh(PMe3)x (1, x = 2; 4, x = 3) and (1,2,3-η3)-(5-tert-butylazapentadienyl)Ir(PEt3)x (7, x = 2; 12, x = 3), which are produced by reacting [(cyclooctene)2M(μ-Cl)]2 with the appropriate amount of phosphine, followed by potassium tert-butylazapentadienide. Each of these Compounds reacts with 1 equivalent of triflic acid to produce a monoprotonation product. Rhodium Compounds 1 and 4 react at nitrogen to produce 2 and 5, respectively. Iridium Compound 7 reacts at the metal center, generating an Iridium-hydride product, 8, in which the azapentadienyl ligand coordinates in an unusual η3, η1-fashion, while Compound 12 reacts at nitrogen to produce 13. The monoprotonation products have been treated with additional acid, and in each case the secondary site of electrophilic addition has been determined. Rhodium Compounds 2 and 5 both react with a second equivalent of triflic acid at the metal center to produce...
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Synthesis, Spectroscopy, Structure, and Reactivity of Azapentadienyl-Rhodium-Phosphine and Azapentadienyl-Iridium-Phosphine Complexes1
Organometallics, 2013Co-Authors: John R. Bleeke, Wipark Anutrasakda, Nigam P. RathAbstract:We report the synthesis, spectroscopy, structure, and reactivity of (1,2,3-η3)-(5-tert-butylazapentadienyl)Rh(PMe3)x (1, x = 2; 4, x = 3) and (1,2,3-η3)-(5-tert-butylazapentadienyl)Ir(PEt3)x (7, x = 2; 12, x = 3), which are produced by reacting [(cyclooctene)2M(μ-Cl)]2 with the appropriate amount of phosphine, followed by potassium tert-butylazapentadienide. Each of these Compounds reacts with 1 equivalent of triflic acid to produce a monoprotonation product. Rhodium Compounds 1 and 4 react at nitrogen to produce 2 and 5, respectively. Iridium Compound 7 reacts at the metal center, generating an Iridium-hydride product, 8, in which the azapentadienyl ligand coordinates in an unusual η3, η1-fashion, while Compound 12 reacts at nitrogen to produce 13. The monoprotonation products have been treated with additional acid, and in each case the secondary site of electrophilic addition has been determined. Rhodium Compounds 2 and 5 both react with a second equivalent of triflic acid at the metal center to produce...
And Satoshi Sakaguchi - One of the best experts on this subject based on the ideXlab platform.
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Catalytic Reductive Alkylation of Secondary Amine with Aldehyde and Silane by an Iridium Compound
The Journal of organic chemistry, 2005Co-Authors: Tomoya Mizuta, And Satoshi Sakaguchi, Yasutaka IshiiAbstract:An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an Iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75 °C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of Iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an Iridium catalyst to afford the corresponding tertiary amines in good to excellent y...
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catalytic reductive alkylation of secondary amine with aldehyde and silane by an Iridium Compound
Journal of Organic Chemistry, 2005Co-Authors: Tomoya Mizuta, And Satoshi Sakaguchi, Yasutaka IshiiAbstract:An efficient methodology for the reductive alkylation of secondary amine with aldehyde and Et3SiH using an Iridium complex as a catalyst has been developed. For example, treatment of dibutylamine with butyraldehyde and Et3SiH (a 1:1:1 molar amount of amine, aldehyde, and silane) in 1,4-dioxane at 75 °C under the influence of a catalytic amount of [IrCl(cod)]2 gave tributylamine in quantitative yield. In this reaction, no reduction of aldehyde took place. It was found that IrCl3, which is a starting material for preparation of Iridium complexes such as [IrCl(cod)]2, acts as an efficient catalyst for the present reductive alkylation of amine. In addition, a cheaper, easy-to-handle, and environmentally friendly reducing reagent such as polymethylhydrosiloxane (PMHS) in place of Et3SiH was also useful. Thus, a variety of secondary amines could be alkylated by allowing them to react with aldehydes and PMHS in the presence of an Iridium catalyst to afford the corresponding tertiary amines in good to excellent y...