Organophotocatalytic Carbamoylation of Morita-Baylis-Hillman Carbonates

Lucas Marchini; Jeimy A.C. Vélez; Elias Andre; Jose Tiago M. Correia; Sidnei Moura; Márcio W. Paixão

doi:10.1002/adsc.202301419

Organophotocatalytic Carbamoylation of Morita-Baylis-Hillman Carbonates

Lucas Marchini, Jeimy A.C. Vélez, Elias Andre, Jose Tiago M. Correia^*, Sidnei Moura, Márcio W. Paixão^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Herein, we demonstrate that carbamoyl radicals generated through an organophotocatalytic protocol from 4-carbamoyl-dihydropyridines (carbamoyl-DHPs) can be incorporated into Morita-Baylis-Hillman (MBH) carbonates, affording a range of polyfunctionalized scaffolds with yields ranging from 63–98%. Reaction monitoring experiments, scale-up, reuse of the organophotocatalyst, and the hydrogenation of the succinamic ester's alkene moiety was also conducted, in order to showcase the mechanistic features and the robustness of this photochemical protocol.

Original language	English
Journal	Advanced Synthesis and Catalysis
Number of pages	10
ISSN	1615-4150
DOIs	https://doi.org/10.1002/adsc.202301419
Publication status	Accepted/In press - 2024

Keywords

Carbamoyl Radicals
Isomerization
Morita-Baylis-Hillman adducts
Organophotocatalyst
Visible-light

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title = "Organophotocatalytic Carbamoylation of Morita-Baylis-Hillman Carbonates",

abstract = "Herein, we demonstrate that carbamoyl radicals generated through an organophotocatalytic protocol from 4-carbamoyl-dihydropyridines (carbamoyl-DHPs) can be incorporated into Morita-Baylis-Hillman (MBH) carbonates, affording a range of polyfunctionalized scaffolds with yields ranging from 63–98%. Reaction monitoring experiments, scale-up, reuse of the organophotocatalyst, and the hydrogenation of the succinamic ester's alkene moiety was also conducted, in order to showcase the mechanistic features and the robustness of this photochemical protocol.",

keywords = "Carbamoyl Radicals, Isomerization, Morita-Baylis-Hillman adducts, Organophotocatalyst, Visible-light",

author = "Lucas Marchini and V{\'e}lez, {Jeimy A.C.} and Elias Andre and Correia, {Jose Tiago M.} and Sidnei Moura and Paix{\~a}o, {M{\'a}rcio W.}",

note = "Publisher Copyright: {\textcopyright} 2024 Wiley-VCH GmbH.",

year = "2024",

doi = "10.1002/adsc.202301419",

language = "English",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

}

TY - JOUR

T1 - Organophotocatalytic Carbamoylation of Morita-Baylis-Hillman Carbonates

AU - Marchini, Lucas

AU - Vélez, Jeimy A.C.

AU - Andre, Elias

AU - Correia, Jose Tiago M.

AU - Moura, Sidnei

AU - Paixão, Márcio W.

PY - 2024

Y1 - 2024

N2 - Herein, we demonstrate that carbamoyl radicals generated through an organophotocatalytic protocol from 4-carbamoyl-dihydropyridines (carbamoyl-DHPs) can be incorporated into Morita-Baylis-Hillman (MBH) carbonates, affording a range of polyfunctionalized scaffolds with yields ranging from 63–98%. Reaction monitoring experiments, scale-up, reuse of the organophotocatalyst, and the hydrogenation of the succinamic ester's alkene moiety was also conducted, in order to showcase the mechanistic features and the robustness of this photochemical protocol.

AB - Herein, we demonstrate that carbamoyl radicals generated through an organophotocatalytic protocol from 4-carbamoyl-dihydropyridines (carbamoyl-DHPs) can be incorporated into Morita-Baylis-Hillman (MBH) carbonates, affording a range of polyfunctionalized scaffolds with yields ranging from 63–98%. Reaction monitoring experiments, scale-up, reuse of the organophotocatalyst, and the hydrogenation of the succinamic ester's alkene moiety was also conducted, in order to showcase the mechanistic features and the robustness of this photochemical protocol.

KW - Carbamoyl Radicals

KW - Isomerization

KW - Morita-Baylis-Hillman adducts

KW - Organophotocatalyst

KW - Visible-light

U2 - 10.1002/adsc.202301419

DO - 10.1002/adsc.202301419

M3 - Journal article

AN - SCOPUS:85188183198

SN - 1615-4150

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

ER -

Organophotocatalytic Carbamoylation of Morita-Baylis-Hillman Carbonates

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