Home > Research > Publications & Outputs > Optimizing the Mizoroki–Heck reaction of cyclic...

Associated organisational unit

Electronic data

  • Cyclic_allyl_amine_Heck_Final_Draft

    Rights statement: This is the author’s version of a work that was accepted for publication in Journal of Catalysis. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Catalysis, 360, 2018 DOI: 10.1016/j.jcat.2018.01.007

    Accepted author manuscript, 496 KB, PDF document

    Available under license: CC BY-NC-ND: Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License

Links

Text available via DOI:

View graph of relations

Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups

Research output: Contribution to Journal/MagazineJournal articlepeer-review

Published

Standard

Optimizing the Mizoroki–Heck reaction of cyclic allyl amines : Gram-scale synthesis of preclamol without protecting groups. / Sweeney, Joseph Bernard; Adams, Kirsty; Doulcet, Julien et al.

In: Journal of Catalysis, Vol. 360, 04.2018, p. 97-101.

Research output: Contribution to Journal/MagazineJournal articlepeer-review

Harvard

APA

Vancouver

Sweeney JB, Adams K, Doulcet J, Thapa B, Tran F, Crook R. Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups. Journal of Catalysis. 2018 Apr;360:97-101. Epub 2018 Feb 22. doi: 10.1016/j.jcat.2018.01.007

Author

Sweeney, Joseph Bernard ; Adams, Kirsty ; Doulcet, Julien et al. / Optimizing the Mizoroki–Heck reaction of cyclic allyl amines : Gram-scale synthesis of preclamol without protecting groups. In: Journal of Catalysis. 2018 ; Vol. 360. pp. 97-101.

Bibtex

@article{4d36ed61dd874c618d3747aac69ba0c3,
title = "Optimizing the Mizoroki–Heck reaction of cyclic allyl amines: Gram-scale synthesis of preclamol without protecting groups",
abstract = "Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligating heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underexplored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of our study designed to deliver an optimized, scalable MH procedure for N-alkyltetrahydropyridines and its exemplification in a gram-scale synthesis of the drug substance preclamol.",
keywords = "Catalysis, Tetrahydropyridines, Mizoroki–Heck reaction, Aryl piperidines, CNS drugs",
author = "Sweeney, {Joseph Bernard} and Kirsty Adams and Julien Doulcet and Bimod Thapa and Fanny Tran and Robert Crook",
note = "This is the author{\textquoteright}s version of a work that was accepted for publication in Journal of Catalysis. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Catalysis, 360, 2018 DOI: 10.1016/j.jcat.2018.01.007",
year = "2018",
month = apr,
doi = "10.1016/j.jcat.2018.01.007",
language = "English",
volume = "360",
pages = "97--101",
journal = "Journal of Catalysis",
issn = "0021-9517",
publisher = "Academic Press Inc.",

}

RIS

TY - JOUR

T1 - Optimizing the Mizoroki–Heck reaction of cyclic allyl amines

T2 - Gram-scale synthesis of preclamol without protecting groups

AU - Sweeney, Joseph Bernard

AU - Adams, Kirsty

AU - Doulcet, Julien

AU - Thapa, Bimod

AU - Tran, Fanny

AU - Crook, Robert

N1 - This is the author’s version of a work that was accepted for publication in Journal of Catalysis. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Catalysis, 360, 2018 DOI: 10.1016/j.jcat.2018.01.007

PY - 2018/4

Y1 - 2018/4

N2 - Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligating heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underexplored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of our study designed to deliver an optimized, scalable MH procedure for N-alkyltetrahydropyridines and its exemplification in a gram-scale synthesis of the drug substance preclamol.

AB - Though a widely used metal-catalyzed cross-coupling process, the Mizoroki–Heck (MH) reaction can be a capricious transformation. This is particularly true for oxidation-prone alkene substrates containing ligating heteroatoms, as in the case of N-alkyl tetrahydropyridines, whose MH reactions have been underexplored due to the many side reactions that hamper the process. Since the products of tetrahydropyridine Heck reactions are direct precursors to potent pharmacophores, and therefore of commercial value, this is a significant drawback. We report here the results of our study designed to deliver an optimized, scalable MH procedure for N-alkyltetrahydropyridines and its exemplification in a gram-scale synthesis of the drug substance preclamol.

KW - Catalysis

KW - Tetrahydropyridines

KW - Mizoroki–Heck reaction

KW - Aryl piperidines

KW - CNS drugs

U2 - 10.1016/j.jcat.2018.01.007

DO - 10.1016/j.jcat.2018.01.007

M3 - Journal article

VL - 360

SP - 97

EP - 101

JO - Journal of Catalysis

JF - Journal of Catalysis

SN - 0021-9517

ER -