Continuous flow organocatalyzed methoxycarbonylation of benzyl alcohol derivatives with dimethyl carbonate

Toupy, Thomas; Bovy, Loïc; Monbaliu, Jean-Christophe

doi:10.1007/s41981-022-00216-2

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Continuous flow organocatalyzed methoxycarbonylation of benzyl alcohol derivatives with dimethyl carbonate

Toupy, Thomas; Bovy, Loïc; Monbaliu, Jean-Christophe

2022 • In Journal of Flow Chemistry

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https://hdl.handle.net/2268/288627

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10.1007/s41981-022-00216-2

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Keywords :

Organic Chemistry; Carbonation; Continuous Flow; Benzyl alcohol; Hydroxycarbamates

Abstract :

[en] An organocatalytic continuous flow process is presented for the preparation of non-symmetric benzyl carbonate derivatives. The procedure relies on dimethyl carbonate as a reagent and a solvent in conjunction with an organocatalyst for the selective methoxycarbonylation of diversely substituted benzylic alcohols. The reaction is optimized with benzyl alcohol as a model substrate, which emphasizes 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (Verkade’s base) and phosphazene base P2-Et as suitable organocatalysts. The optimized conditions are next extended to a small library of 18 structurally diverse benzylic alcohol derivatives. High conversion (66–96%) and total selectivity (>99%) are achieved under mild conditions and short residence time, which converge toward a versatile and robust continuous flow protocol. Then, we illustrate that a set of representative benzyl methyl carbonates can be considered as stable, low toxicity surrogates of the corresponding chloroformates for the preparation of valuable benzyl N-hydroxycarbamates.

Disciplines :

Chemistry

Author, co-author :

Toupy, Thomas ; Université de Liège - ULiège > Molecular Systems (MolSys)

Bovy, Loïc ; Université de Liège - ULiège > Molecular Systems (MolSys)

Monbaliu, Jean-Christophe ; Université de Liège - ULiège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis

Language :

English

Title :

Continuous flow organocatalyzed methoxycarbonylation of benzyl alcohol derivatives with dimethyl carbonate

Publication date :

02 March 2022

Journal title :

Journal of Flow Chemistry

ISSN :

2062-249X

eISSN :

2063-0212

Publisher :

Springer Science and Business Media LLC

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://link.springer.com/content/pdf/10.1007/s41981-022-00216-2.pdf

Funders :

FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture

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since 07 March 2022

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