Manganese catalysed dehydrogenative synthesis of polyureas from diformamide and diamines

Angus  McLuskie; Claire N. Brodie; Michele  Tricarico; Chang Gao; Gavin Peters; Aaron B. Naden; C. Logan Mackay; Jin-Chong Tan; Amit Kumar

doi:10.1039/D3CY00284E

Manganese catalysed dehydrogenative synthesis of polyureas from diformamide and diamines

Angus McLuskie, Claire N. Brodie, Michele Tricarico, Chang Gao, Gavin Peters, Aaron B. Naden, C. Logan Mackay, Jin-Chong Tan^*, Amit Kumar^*

^*Corresponding author for this work

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

Abstract

We report here the synthesis of polyureas from the dehydrogenative coupling of diamines and diformamides. The reaction is catalysed by a manganese pincer complex and releases H₂ gas as the only by-product making the process atom-economic and sustainable. The reported method is greener in comparison to the current state-of-the-art production routes that involve diisocyanate and phosgene feedstock. We also report here the physical, morphological, and mechanical properties of synthesized polyureas. Based on our mechanistic studies, we suggest that the reaction proceeds via isocyanate intermediates formed by the manganese catalysed dehydrogenation of formamides.

Original language	English
Pages (from-to)	3551-3557
Number of pages	7
Journal	Catalysis Science & Technology
Volume	13
Issue number	12
Early online date	15 May 2023
DOIs	https://doi.org/10.1039/D3CY00284E
Publication status	Published - 21 Jun 2023

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New Directions for the Sythesis: New Directions for the Synthesis and Degradation of Renewable and Recyclable Plastics Using Homogeneous Catalytic (De)hydrogenation
Kumar, A. (PI)
Medical Research Council
1/08/22 → 31/07/26
Project: Fellowship
Light Element Analysis Facility (LEAF): Light Element Analysis Facility (LEAF)
Irvine, J. T. S. (PI), Baker, R. (CoI) & Miller, D. N. (CoI)
EPSRC
5/04/20 → 4/04/23
Project: Standard
Electon Microscopy: Electon Microscopy for the characterisation and manipulation of advanced function materials and their interfaces at the nanoscale
Irvine, J. T. S. (PI), Baker, R. (CoI) & Zhou, W. (CoI)
EPSRC
1/04/18 → 2/09/20
Project: Standard

Manganese Catalysed Dehydrogenative Synthesis of Polyureas from Diformamide and Diamines (dataset)
McLuskie, A. (Creator), Brodie, C. N. (Creator), Tricarico, M. (Contributor), Gao, C. (Contributor), Peters, G. (Contributor), Naden, A. B. (Contributor), Mackay, C. L. (Contributor), Tan, J.-C. (Contributor) & Kumar, A. (Creator), University of St Andrews, 18 May 2023
DOI: 10.17630/36c115ac-4dbb-4a87-a3e9-c042f8f1a91e
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Cite this

@article{6441b68d92384108806cd7594cf0ffac,

title = "Manganese catalysed dehydrogenative synthesis of polyureas from diformamide and diamines",

abstract = "We report here the synthesis of polyureas from the dehydrogenative coupling of diamines and diformamides. The reaction is catalysed by a manganese pincer complex and releases H2 gas as the only by-product making the process atom-economic and sustainable. The reported method is greener in comparison to the current state-of-the-art production routes that involve diisocyanate and phosgene feedstock. We also report here the physical, morphological, and mechanical properties of synthesized polyureas. Based on our mechanistic studies, we suggest that the reaction proceeds via isocyanate intermediates formed by the manganese catalysed dehydrogenation of formamides.",

author = "Angus McLuskie and Brodie, {Claire N.} and Michele Tricarico and Chang Gao and Gavin Peters and Naden, {Aaron B.} and Mackay, {C. Logan} and Jin-Chong Tan and Amit Kumar",

note = "Funding: Authors acknowledge the funding from UKRI Future Leaders Fellowship (MR/W007460/1). A.M. thanks the University of St Andrews (Impact & Innovation Fund) for funding. M.T. and J.C.T. thank the ERC Consolidator Grant (PROMOFS grant agreement 771575) for funding the research. ABN gratefully acknowledges funding from the EPSRC through grant numbers EP/L017008/1, EP/R023751/1 and EP/T019298/1.",

year = "2023",

month = jun,

day = "21",

doi = "10.1039/D3CY00284E",

language = "English",

volume = "13",

pages = "3551--3557",

journal = "Catalysis Science & Technology",

issn = "2044-4753",

publisher = "Royal Society of Chemistry",

number = "12",

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TY - JOUR

T1 - Manganese catalysed dehydrogenative synthesis of polyureas from diformamide and diamines

AU - McLuskie, Angus

AU - Brodie, Claire N.

AU - Tricarico, Michele

AU - Gao, Chang

AU - Peters, Gavin

AU - Naden, Aaron B.

AU - Mackay, C. Logan

AU - Tan, Jin-Chong

AU - Kumar, Amit

N1 - Funding: Authors acknowledge the funding from UKRI Future Leaders Fellowship (MR/W007460/1). A.M. thanks the University of St Andrews (Impact & Innovation Fund) for funding. M.T. and J.C.T. thank the ERC Consolidator Grant (PROMOFS grant agreement 771575) for funding the research. ABN gratefully acknowledges funding from the EPSRC through grant numbers EP/L017008/1, EP/R023751/1 and EP/T019298/1.

PY - 2023/6/21

Y1 - 2023/6/21

N2 - We report here the synthesis of polyureas from the dehydrogenative coupling of diamines and diformamides. The reaction is catalysed by a manganese pincer complex and releases H2 gas as the only by-product making the process atom-economic and sustainable. The reported method is greener in comparison to the current state-of-the-art production routes that involve diisocyanate and phosgene feedstock. We also report here the physical, morphological, and mechanical properties of synthesized polyureas. Based on our mechanistic studies, we suggest that the reaction proceeds via isocyanate intermediates formed by the manganese catalysed dehydrogenation of formamides.

AB - We report here the synthesis of polyureas from the dehydrogenative coupling of diamines and diformamides. The reaction is catalysed by a manganese pincer complex and releases H2 gas as the only by-product making the process atom-economic and sustainable. The reported method is greener in comparison to the current state-of-the-art production routes that involve diisocyanate and phosgene feedstock. We also report here the physical, morphological, and mechanical properties of synthesized polyureas. Based on our mechanistic studies, we suggest that the reaction proceeds via isocyanate intermediates formed by the manganese catalysed dehydrogenation of formamides.

U2 - 10.1039/D3CY00284E

DO - 10.1039/D3CY00284E

M3 - Article

SN - 2044-4753

VL - 13

SP - 3551

EP - 3557

JO - Catalysis Science & Technology

JF - Catalysis Science & Technology

IS - 12

ER -

Manganese catalysed dehydrogenative synthesis of polyureas from diformamide and diamines

Abstract

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Projects

New Directions for the Sythesis: New Directions for the Synthesis and Degradation of Renewable and Recyclable Plastics Using Homogeneous Catalytic (De)hydrogenation

Light Element Analysis Facility (LEAF): Light Element Analysis Facility (LEAF)

Electon Microscopy: Electon Microscopy for the characterisation and manipulation of advanced function materials and their interfaces at the nanoscale

Datasets

Manganese Catalysed Dehydrogenative Synthesis of Polyureas from Diformamide and Diamines (dataset)

Cite this