Additive Effects of Amines on Asymmetric Hydrogenation of Quinoxalines Catalyzed by Chiral Iridium Complexes
The additive effects of amines were realized in the asymmetric hydrogenation of 2‐phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide‐bridged iridium complexes [{Ir(H)[diphosphine]}2(μ‐X)3]X (diphosphine=(S)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl [(S)‐BI...
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| Published in | Chemistry : a European journal Vol. 18; no. 37; pp. 11578 - 11592 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
10.09.2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| Abstract | The additive effects of amines were realized in the asymmetric hydrogenation of 2‐phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide‐bridged iridium complexes [{Ir(H)[diphosphine]}2(μ‐X)3]X (diphosphine=(S)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl [(S)‐BINAP], (S)‐5,5′‐bis(diphenylphosphino)‐4,4′‐bi‐1,3‐benzodioxole [(S)‐SEGPHOS], (S)‐5,5′‐bis(diphenylphosphino)‐2,2,2′,2′‐tetrafluoro‐4,4′‐bi‐1,3‐benzodioxole [(S)‐DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2‐aryl‐1,2,3,4‐tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N‐methyl‐p‐anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate‐coordinated mononuclear complex [IrHCl2(2‐phenylquinoxaline){(S)‐BINAP}], which afforded half‐reduced product 3‐phenyl‐1,2‐dihydroquinoxaline. A poorly enantioselective disproportionation of this half‐reduced product afforded (S)‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline. The other cycle involved a more active hydride–amide catalyst, derived from amine‐coordinated mononuclear complex [IrCl2H(MPA){(S)‐BINAP}], which functioned to reduce 2‐phenylquinoxaline to (S)‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an IrI–JOSIPHOS (JOSIPHOS=(R)‐1‐[(Sp)‐2‐(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2‐phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive‐feedback effect from the product amines.
Additive effects were investigated in the asymmetric hydrogenation of 2‐substituted quinoxalines catalyzed by a chiral iridium complex (see scheme). Catalytic activity and enantioselectivity were improved by the addition of an aniline derivatives and product amine. |
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| AbstractList | The additive effects of amines were realized in the asymmetric hydrogenation of 2-phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide-bridged iridium complexes [{Ir(H)[diphosphine]}(2)(μ-X)(3)]X (diphosphine = (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(S)-BINAP], (S)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole [(S)-SEGPHOS], (S)-5,5'-bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole [(S)-DIFLUORPHOS]; X = Cl, Br, I) to produce the corresponding 2-aryl-1,2,3,4-tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N-methyl-p-anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate-coordinated mononuclear complex [IrHCl(2)(2-phenylquinoxaline){(S)-BINAP}], which afforded half-reduced product 3-phenyl-1,2-dihydroquinoxaline. A poorly enantioselective disproportionation of this half-reduced product afforded (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline. The other cycle involved a more active hydride-amide catalyst, derived from amine-coordinated mononuclear complex [IrCl(2)H(MPA){(S)-BINAP}], which functioned to reduce 2-phenylquinoxaline to (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an Ir(I)-JOSIPHOS (JOSIPHOS = (R)-1-[(S(p))-2-(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2-phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive-feedback effect from the product amines. The additive effects of amines were realized in the asymmetric hydrogenation of 2-phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide-bridged iridium complexes [{Ir(H)[diphosphine]}2(mu-X)3]X (diphosphine=(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(S)-BINAP], (S)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole [(S)-SEGPHOS], (S)-5,5'-bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole [(S)-DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2-aryl-1,2,3,4-tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N-methyl-p-anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate-coordinated mononuclear complex [IrHCl2(2-phenylquinoxaline){(S)-BINAP}], which afforded half-reduced product 3-phenyl-1,2-dihydroquinoxaline. A poorly enantioselective disproportionation of this half-reduced product afforded (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline. The other cycle involved a more active hydrideamide catalyst, derived from amine-coordinated mononuclear complex [IrCl2H(MPA){(S)-BINAP}], which functioned to reduce 2-phenylquinoxaline to (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an IrIJOSIPHOS (JOSIPHOS=(R)-1-[(Sp)-2-(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2-phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive-feedback effect from the product amines. Abstract The additive effects of amines were realized in the asymmetric hydrogenation of 2‐phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide‐bridged iridium complexes [{Ir(H)[diphosphine]} 2 (μ‐X) 3 ]X (diphosphine=( S )‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl [( S )‐BINAP], ( S )‐5,5′‐bis(diphenylphosphino)‐4,4′‐bi‐1,3‐benzodioxole [( S )‐SEGPHOS], ( S )‐5,5′‐bis(diphenylphosphino)‐2,2,2′,2′‐tetrafluoro‐4,4′‐bi‐1,3‐benzodioxole [( S )‐DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2‐aryl‐1,2,3,4‐tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N ‐methyl‐ p ‐anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of ( S )‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate‐coordinated mononuclear complex [IrHCl 2 (2‐phenylquinoxaline){( S )‐BINAP}], which afforded half‐reduced product 3‐phenyl‐1,2‐dihydroquinoxaline. A poorly enantioselective disproportionation of this half‐reduced product afforded ( S )‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline. The other cycle involved a more active hydride–amide catalyst, derived from amine‐coordinated mononuclear complex [IrCl 2 H(MPA){( S )‐BINAP}], which functioned to reduce 2‐phenylquinoxaline to ( S )‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an Ir I –JOSIPHOS (JOSIPHOS=( R )‐1‐[( S p )‐2‐(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2‐phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive‐feedback effect from the product amines. The additive effects of amines were realized in the asymmetric hydrogenation of 2‐phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide‐bridged iridium complexes [{Ir(H)[diphosphine]}2(μ‐X)3]X (diphosphine=(S)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl [(S)‐BINAP], (S)‐5,5′‐bis(diphenylphosphino)‐4,4′‐bi‐1,3‐benzodioxole [(S)‐SEGPHOS], (S)‐5,5′‐bis(diphenylphosphino)‐2,2,2′,2′‐tetrafluoro‐4,4′‐bi‐1,3‐benzodioxole [(S)‐DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2‐aryl‐1,2,3,4‐tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N‐methyl‐p‐anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate‐coordinated mononuclear complex [IrHCl2(2‐phenylquinoxaline){(S)‐BINAP}], which afforded half‐reduced product 3‐phenyl‐1,2‐dihydroquinoxaline. A poorly enantioselective disproportionation of this half‐reduced product afforded (S)‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline. The other cycle involved a more active hydride–amide catalyst, derived from amine‐coordinated mononuclear complex [IrCl2H(MPA){(S)‐BINAP}], which functioned to reduce 2‐phenylquinoxaline to (S)‐2‐phenyl‐1,2,3,4‐tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an IrI–JOSIPHOS (JOSIPHOS=(R)‐1‐[(Sp)‐2‐(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2‐phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive‐feedback effect from the product amines. Additive effects were investigated in the asymmetric hydrogenation of 2‐substituted quinoxalines catalyzed by a chiral iridium complex (see scheme). Catalytic activity and enantioselectivity were improved by the addition of an aniline derivatives and product amine. The additive effects of amines were realized in the asymmetric hydrogenation of 2-phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide-bridged iridium complexes [{Ir(H)[diphosphine]} sub(2)( mu -X) sub(3)]X (diphosphine=(S)-2,2'-bis(diphenylphosphino )-1,1'-binaphthyl [(S)-BINAP], (S)-5,5'-bis(diphenylphosphino)-4,4' -bi-1,3-benzodioxole [(S)-SEGPHOS], (S)-5,5'-bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1 ,3-benzodioxole [(S)-DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2-aryl-1,2,3,4-tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N-methyl-p-anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate-coordinated mononuclear complex [IrHCl sub(2)(2-phenylquinoxaline){(S)-BINAP}], which afforded half-reduced product 3-phenyl-1,2-dihydroquinoxaline. A poorly enantioselective disproportionation of this half-reduced product afforded (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline. The other cycle involved a more active hydride-amide catalyst, derived from amine-coordinated mononuclear complex [IrCl sub(2)H(MPA){(S)-BINAP}], which functioned to reduce 2-phenylquinoxaline to (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an Ir super(I)-JOSIPHOS (JOSIPHOS=(R)-1-[(S sub(p))- 2-(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2-phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive-feedback effect from the product amines. Additive effects were investigated in the asymmetric hydrogenation of 2-substituted quinoxalines catalyzed by a chiral iridium complex (see scheme). Catalytic activity and enantioselectivity were improved by the addition of an aniline derivatives and product amine. The additive effects of amines were realized in the asymmetric hydrogenation of 2-phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide-bridged iridium complexes [{Ir(H)[diphosphine]}2(µ-X)3]X (diphosphine=(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(S)-BINAP], (S)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole [(S)-SEGPHOS], (S)-5,5'-bis(diphenylphosphino)-2,2,2',2'-tetrafluoro-4,4'-bi-1,3-benzodioxole [(S)-DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2-aryl-1,2,3,4-tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N-methyl-p-anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate-coordinated mononuclear complex [IrHCl2(2-phenylquinoxaline){(S)-BINAP}], which afforded half-reduced product 3-phenyl-1,2-dihydroquinoxaline. A poorly enantioselective disproportionation of this half-reduced product afforded (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline. The other cycle involved a more active hydride-amide catalyst, derived from amine-coordinated mononuclear complex [IrCl2H(MPA){(S)-BINAP}], which functioned to reduce 2-phenylquinoxaline to (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an IrI-JOSIPHOS (JOSIPHOS=(R)-1-[(Sp)-2-(dicyclohexylphosphino)ferrocenylethyl]diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2-phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive-feedback effect from the product amines. |
| Author | Ohshima, Takashi Nagano, Takuto Iimuro, Atsuhiro Kita, Yusuke Schwenk, Rino Mashima, Kazushi Togni, Antonio |
| Author_xml | – sequence: 1 givenname: Takuto surname: Nagano fullname: Nagano, Takuto organization: Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8631 (Japan), Fax: (+81) 6-6850-6245 – sequence: 2 givenname: Atsuhiro surname: Iimuro fullname: Iimuro, Atsuhiro organization: Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8631 (Japan), Fax: (+81) 6-6850-6245 – sequence: 3 givenname: Rino surname: Schwenk fullname: Schwenk, Rino organization: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland) – sequence: 4 givenname: Takashi surname: Ohshima fullname: Ohshima, Takashi organization: Graduate School of Pharmaceutical Sciences, Kyushu University, CREST, Maidashi Higashi-ku, Fukuoka 812-8582 (Japan) – sequence: 5 givenname: Yusuke surname: Kita fullname: Kita, Yusuke organization: Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8631 (Japan), Fax: (+81) 6-6850-6245 – sequence: 6 givenname: Antonio surname: Togni fullname: Togni, Antonio organization: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, 8093 Zürich (Switzerland) – sequence: 7 givenname: Kazushi surname: Mashima fullname: Mashima, Kazushi email: Mashima@chem.es.osaka-u.ac.jp organization: Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8631 (Japan), Fax: (+81) 6-6850-6245 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22915378$$D View this record in MEDLINE/PubMed |
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| Keywords | PYRIDINE-DERIVATIVES reaction mechanisms asymmetric catalysis hydrogenation HETEROAROMATIC-COMPOUNDS AUTOCATALYTIC REACTION iridium HOMOGENEOUS HYDROGENATION HIGHLY ENANTIOSELECTIVE HYDROGENATION DIPHOSPHINE LIGANDS nitrogen heterocycles QUINOLINE DERIVATIVES BISPHOSPHINE LIGANDS ORGANOCATALYTIC TRANSFER HYDROGENATION IMINE HYDROGENATION |
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| Snippet | The additive effects of amines were realized in the asymmetric hydrogenation of 2‐phenylquinoxaline, and its derivatives, catalyzed by chiral cationic... The additive effects of amines were realized in the asymmetric hydrogenation of 2-phenylquinoxaline, and its derivatives, catalyzed by chiral cationic... Abstract The additive effects of amines were realized in the asymmetric hydrogenation of 2‐phenylquinoxaline, and its derivatives, catalyzed by chiral cationic... |
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| SubjectTerms | Additives Amines Amines - chemical synthesis Amines - chemistry asymmetric catalysis Asymmetry Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Derivatives Hydrogenation iridium Iridium - chemistry Iridium compounds Molecular Structure nitrogen heterocycles Organometallic Compounds - chemistry Physical Sciences Quinoxalines Quinoxalines - chemistry reaction mechanisms Science & Technology |
| Title | Additive Effects of Amines on Asymmetric Hydrogenation of Quinoxalines Catalyzed by Chiral Iridium Complexes |
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