Manganese catalysed dehydrogenative synthesis of polyureas from diformamide and diamines

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

doi:10.1039/d3cy00284e

Cited by 1 publication

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“…18 The synthesis of polyamides has been reported from the dehydrogenative coupling of diols and diamines by Guan 19 and Milstein. 20 We, [21][22][23] Robertson, 24 and Liu 25 have independently reported on the synthesis of polyureas from the coupling of diamines with methanol or diformamides using ruthenium or manganese pincer catalysts. We have also recently reported the synthesis of polyethyleneimine derivatives from the manganese catalysed coupling of ethylene glycol and ethylenediamine.…”

Section: Introductionmentioning

confidence: 99%

Exploiting Decarbonylation and Dehydrogenation of Forma-mides for the Synthesis of Ureas, Polyureas, and Poly(urea-urethanes)

Luk,

Goodfellow,

et al. 2024

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Urea derivatives, polyureas, and poly(urea-urethanes) are materials of great interest. However, their current methods of syn-thesis involve toxic feedstock - isocyanate and phosgene gas. There is a significant interest in developing alternative meth-odologies for their synthesis from safer feedstock. We report here new methods for the synthesis of urea derivatives, polyure-as, and polyurea(urethane) using a ruthenium pincer catalyst. In this approach, urea derivatives and polyureas are synthesized from the self-coupling of formamides and diformamides, respectively, whereas polyurea(urethanes) are synthesized from the coupling of diformamides and diols. CO and H2 gases are eliminated in all these processes. Decarbonylation of formamides using such organometallic catalysts has not been reported before and therefore mechanistic insights have been provided using experiments and DFT computation to shed light on pathways of these processes.

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Section: Introductionmentioning

confidence: 99%

Exploiting Decarbonylation and Dehydrogenation of Forma-mides for the Synthesis of Ureas, Polyureas, and Poly(urea-urethanes)

Luk,

Goodfellow,

et al. 2024

Preprint

View full text Add to dashboard Cite

show abstract

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...

Cited by 1 publication

References 40 publications

Exploiting Decarbonylation and Dehydrogenation of Forma-mides for the Synthesis of Ureas, Polyureas, and Poly(urea-urethanes)

Exploiting Decarbonylation and Dehydrogenation of Forma-mides for the Synthesis of Ureas, Polyureas, and Poly(urea-urethanes)

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