Unveiling the impact of a CF2 motif in the isothiourea catalyst skeleton: evaluating C(3)-F2-HBTM and its catalytic activity

Matthew Westwood; Kevin Kasten; Lotte Stockhammer; Roberto del Río-Rodríguez; Jose A. Fernández-Salas; Andreas Eitzinger; Alexandra M. Z. Slawin; Mario Waser; Jose Alémán; Armin R. Ofial; Andrew D. Smith

doi:10.24820/ark.5550190.p012.093

Unveiling the impact of a CF₂ motif in the isothiourea catalyst skeleton: evaluating C(3)-F₂-HBTM and its catalytic activity

Matthew Westwood, Kevin Kasten, Lotte Stockhammer, Roberto del Río-Rodríguez, Jose A. Fernández-Salas, Andreas Eitzinger, Alexandra M. Z. Slawin, Mario Waser, Jose Alémán, Armin R. Ofial^*, Andrew D. Smith^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

The incorporation of the CF₂ motif within organic structures is known to affect the susceptibility of functional groups to oxidation, as well as altering conformation and reactivity. In this manuscript, the incorporation of the CF₂ functional group within an isothiourea catalyst skeleton to give C(3)-F₂-HBTM is reported. Effective gram-scale routes to both racemic and enantiopure heterocyclic Lewis bases are developed, with preliminary catalytic and kinetic activity evaluated.

Original language	English
Article number	202312093
Number of pages	23
Journal	ARKIVOC
Volume	2024
Issue number	4
DOIs	https://doi.org/10.24820/ark.5550190.p012.093
Publication status	Published - 31 Dec 2023

Keywords

Isothiourea
Fluorination
Asymmetric synthesis
Photocatalysis

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10.24820/ark.5550190.p012.093Licence: CC BY

Westwood_2024_Arkivoc_CF2_CCBY
Copyright © 2024 Author(s). Open Access. This paper is an open access article distributed under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Final published version, 1.59 MBLicence: CC BY

Exploiting Chalcogen Bonding and Non: Exploiting Chalcogen Bonding and Non-Covalent Interactions in Isochalcogenourea Catalysis: Catalyst Preparation, Mechanistic Studies and Applications
Smith, A. D. (PI)
1/11/20 → 31/10/23
Project: Standard

Data underpinning "Unveiling the impact of CF2 motif in the Isothiourea Catalyst Skeleton: Evaluating C(3)-F2-HBTM and its Catalytic Activity"
Smith, A. D. (Creator), Westwood, M. (Creator) & Kasten, K. (Creator), University of St Andrews, 25 Sept 2023
DOI: 10.17630/71039bf0-a0c5-44da-9934-0759efd35343
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Westwood, M., Kasten, K., Stockhammer, L., del Río-Rodríguez, R., Fernández-Salas, J. A., Eitzinger, A., Slawin, A. M. Z., Waser, M., Alémán, J., Ofial, A. R., & Smith, A. D. (2023). Unveiling the impact of a CF₂ motif in the isothiourea catalyst skeleton: evaluating C(3)-F₂-HBTM and its catalytic activity. ARKIVOC, 2024(4), Article 202312093. https://doi.org/10.24820/ark.5550190.p012.093

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title = "Unveiling the impact of a CF2 motif in the isothiourea catalyst skeleton: evaluating C(3)-F2-HBTM and its catalytic activity",

abstract = "The incorporation of the CF2 motif within organic structures is known to affect the susceptibility of functional groups to oxidation, as well as altering conformation and reactivity. In this manuscript, the incorporation of the CF2 functional group within an isothiourea catalyst skeleton to give C(3)-F2-HBTM is reported. Effective gram-scale routes to both racemic and enantiopure heterocyclic Lewis bases are developed, with preliminary catalytic and kinetic activity evaluated.",

keywords = "Isothiourea, Fluorination, Asymmetric synthesis, Photocatalysis",

author = "Matthew Westwood and Kevin Kasten and Lotte Stockhammer and {del R{\'i}o-Rodr{\'i}guez}, Roberto and Fern{\'a}ndez-Salas, {Jose A.} and Andreas Eitzinger and Slawin, {Alexandra M. Z.} and Mario Waser and Jose Al{\'e}m{\'a}n and Ofial, {Armin R.} and Smith, {Andrew D.}",

note = "The St Andrews Team (A. D. S., K. K., M. T. W.) thanks the EaSI-CAT centre for Doctoral Training (MTW) and the EPSRC (EP/T023643/1; KK). The Linz team (L. S., A. E., M. W.) gratefully acknowledges generous financial support by the Austrian Science Funds (FWF) through project No. P31784, the Erasmus+ program and the JKU Linz/Upper Austria scheme. The Madrid team (J. A. F.-S., J. A., R. d. R-R.) gratefully acknowledges the Spanish Government (RTI2018-095038-B-100), “Communidad de Madrid” for European Structural Funds (S2018/NMT-4367) and proyectos sinergicos I + D (Y2020/NMT-6469) for funding. J. A. F.-S. thanks the Spanish government for a Ram{\'o}n y Cajal contract.",

year = "2023",

month = dec,

day = "31",

doi = "10.24820/ark.5550190.p012.093",

language = "English",

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Westwood, M, Kasten, K, Stockhammer, L, del Río-Rodríguez, R, Fernández-Salas, JA, Eitzinger, A, Slawin, AMZ, Waser, M, Alémán, J, Ofial, AR & Smith, AD 2023, 'Unveiling the impact of a CF₂ motif in the isothiourea catalyst skeleton: evaluating C(3)-F₂-HBTM and its catalytic activity', ARKIVOC, vol. 2024, no. 4, 202312093. https://doi.org/10.24820/ark.5550190.p012.093

TY - JOUR

T1 - Unveiling the impact of a CF2 motif in the isothiourea catalyst skeleton

T2 - evaluating C(3)-F2-HBTM and its catalytic activity

AU - Westwood, Matthew

AU - Kasten, Kevin

AU - Stockhammer, Lotte

AU - del Río-Rodríguez, Roberto

AU - Fernández-Salas, Jose A.

AU - Eitzinger, Andreas

AU - Slawin, Alexandra M. Z.

AU - Waser, Mario

AU - Alémán, Jose

AU - Ofial, Armin R.

AU - Smith, Andrew D.

N1 - The St Andrews Team (A. D. S., K. K., M. T. W.) thanks the EaSI-CAT centre for Doctoral Training (MTW) and the EPSRC (EP/T023643/1; KK). The Linz team (L. S., A. E., M. W.) gratefully acknowledges generous financial support by the Austrian Science Funds (FWF) through project No. P31784, the Erasmus+ program and the JKU Linz/Upper Austria scheme. The Madrid team (J. A. F.-S., J. A., R. d. R-R.) gratefully acknowledges the Spanish Government (RTI2018-095038-B-100), “Communidad de Madrid” for European Structural Funds (S2018/NMT-4367) and proyectos sinergicos I + D (Y2020/NMT-6469) for funding. J. A. F.-S. thanks the Spanish government for a Ramón y Cajal contract.

PY - 2023/12/31

Y1 - 2023/12/31

N2 - The incorporation of the CF2 motif within organic structures is known to affect the susceptibility of functional groups to oxidation, as well as altering conformation and reactivity. In this manuscript, the incorporation of the CF2 functional group within an isothiourea catalyst skeleton to give C(3)-F2-HBTM is reported. Effective gram-scale routes to both racemic and enantiopure heterocyclic Lewis bases are developed, with preliminary catalytic and kinetic activity evaluated.

AB - The incorporation of the CF2 motif within organic structures is known to affect the susceptibility of functional groups to oxidation, as well as altering conformation and reactivity. In this manuscript, the incorporation of the CF2 functional group within an isothiourea catalyst skeleton to give C(3)-F2-HBTM is reported. Effective gram-scale routes to both racemic and enantiopure heterocyclic Lewis bases are developed, with preliminary catalytic and kinetic activity evaluated.

KW - Isothiourea

KW - Fluorination

KW - Asymmetric synthesis

KW - Photocatalysis

U2 - 10.24820/ark.5550190.p012.093

DO - 10.24820/ark.5550190.p012.093

M3 - Article

SN - 1551-7004

VL - 2024

JO - ARKIVOC

JF - ARKIVOC

IS - 4

M1 - 202312093

ER -

Unveiling the impact of a CF2 motif in the isothiourea catalyst skeleton: evaluating C(3)-F2-HBTM and its catalytic activity

Abstract

Keywords

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Projects

Exploiting Chalcogen Bonding and Non: Exploiting Chalcogen Bonding and Non-Covalent Interactions in Isochalcogenourea Catalysis: Catalyst Preparation, Mechanistic Studies and Applications

Datasets

Data underpinning "Unveiling the impact of CF2 motif in the Isothiourea Catalyst Skeleton: Evaluating C(3)-F2-HBTM and its Catalytic Activity"

Cite this

Unveiling the impact of a CF₂ motif in the isothiourea catalyst skeleton: evaluating C(3)-F₂-HBTM and its catalytic activity