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Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology. / Hamid, M. Haniti S. A.; Allen, C. Liana; Lamb, Gareth W. et al.
In: Journal of the American Chemical Society, Vol. 131, No. 5, 11.02.2009, p. 1766-1774.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Hamid, MHSA, Allen, CL, Lamb, GW, Maxwell, AC, Maytum, H, Watson, AJA & Williams, JMJ 2009, 'Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology', Journal of the American Chemical Society, vol. 131, no. 5, pp. 1766-1774. https://doi.org/10.1021/ja807323a

APA

Hamid, M. H. S. A., Allen, C. L., Lamb, G. W., Maxwell, A. C., Maytum, H., Watson, A. J. A., & Williams, J. M. J. (2009). Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology. Journal of the American Chemical Society, 131(5), 1766-1774. https://doi.org/10.1021/ja807323a

Vancouver

Hamid MHSA, Allen CL, Lamb GW, Maxwell AC, Maytum H, Watson AJA et al. Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology. Journal of the American Chemical Society. 2009 Feb 11;131(5):1766-1774. Epub 2009 Jan 21. doi: 10.1021/ja807323a

Author

Hamid, M. Haniti S. A. ; Allen, C. Liana ; Lamb, Gareth W. et al. / Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 5. pp. 1766-1774.

Bibtex

@article{5164e88c0686409b83bd77fe75a04754,
title = "Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology",
abstract = "The alkylation of amines by alcohols has been achieved using 0.5 mol % [Ru(p-cymene)Cl(2)](2) with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. N-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols require more forcing conditions than primary alcohols but are still effective alkylating agents in the presence of this catalyst.",
keywords = "ASTERISK-IR COMPLEX, DYNAMIC KINETIC RESOLUTION, C BOND FORMATION, DIRECT ALPHA-ALKYLATION, PRIMARY ALCOHOLS, SECONDARY ALCOHOLS, TERTIARY-AMINES, SELECTIVE SYNTHESIS, BENZYL ALCOHOLS, WITTIG REACTION",
author = "Hamid, {M. Haniti S. A.} and Allen, {C. Liana} and Lamb, {Gareth W.} and Maxwell, {Aoife C.} and Hannah Maytum and Watson, {Andrew J. A.} and Williams, {Jonathan M. J.}",
year = "2009",
month = feb,
day = "11",
doi = "10.1021/ja807323a",
language = "English",
volume = "131",
pages = "1766--1774",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "AMER CHEMICAL SOC",
number = "5",

}

RIS

TY - JOUR

T1 - Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology

AU - Hamid, M. Haniti S. A.

AU - Allen, C. Liana

AU - Lamb, Gareth W.

AU - Maxwell, Aoife C.

AU - Maytum, Hannah

AU - Watson, Andrew J. A.

AU - Williams, Jonathan M. J.

PY - 2009/2/11

Y1 - 2009/2/11

N2 - The alkylation of amines by alcohols has been achieved using 0.5 mol % [Ru(p-cymene)Cl(2)](2) with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. N-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols require more forcing conditions than primary alcohols but are still effective alkylating agents in the presence of this catalyst.

AB - The alkylation of amines by alcohols has been achieved using 0.5 mol % [Ru(p-cymene)Cl(2)](2) with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. N-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols require more forcing conditions than primary alcohols but are still effective alkylating agents in the presence of this catalyst.

KW - ASTERISK-IR COMPLEX

KW - DYNAMIC KINETIC RESOLUTION

KW - C BOND FORMATION

KW - DIRECT ALPHA-ALKYLATION

KW - PRIMARY ALCOHOLS

KW - SECONDARY ALCOHOLS

KW - TERTIARY-AMINES

KW - SELECTIVE SYNTHESIS

KW - BENZYL ALCOHOLS

KW - WITTIG REACTION

U2 - 10.1021/ja807323a

DO - 10.1021/ja807323a

M3 - Journal article

VL - 131

SP - 1766

EP - 1774

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 5

ER -