Direct comparison of safer or sustainable alternative dipolar aprotic solvents for use in carbon–carbon bond formation

Suwiwat Sangon; Nontipa Supanchaiyamat; James Richard Sherwood; Rob McElroy; Andrew Hunt

doi:10.1039/D0RE00174K

Direct comparison of safer or sustainable alternative dipolar aprotic solvents for use in carbon–carbon bond formation

Suwiwat Sangon, Nontipa Supanchaiyamat, James Richard Sherwood, Rob McElroy, Andrew Hunt

Chemistry

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

Abstract

There is a lot of interest in the development of new, safer and more sustainable polar aprotic solvents due to their importance in industrial applications and significant safety issues with the most commonly used examples. One such area of application is in pharmaceutically relevant C–C coupling reactions, where polar aprotic solvents are commonly used for solubility and to stabilise reaction intermediates. Although there are now a number of excellent alternatives in the literature, to date they have not been compared in a single study. This study demonstrates the effectiveness of the green solvents N-butylpyrrolidinone (NBP), γ-valerolactone (GVL), propylene carbonate (PC) and dihydrolevoglucosenone (Cyrene) in Heck and Baylis–Hillman reactions. Good conversions and initial rates were observed in GVL and NBP in Heck reactions. Cyrene exhibited high initial rates of reaction and high yields in the Baylis–Hillman reaction. This demonstrates Cyrene to be a promising alternative polar aprotic solvent for this reaction.

Original language	English
Pages (from-to)	1798-1804
Journal	Reaction Chemistry & Engineering
Volume	5
Issue number	9
DOIs	https://doi.org/10.1039/D0RE00174K
Publication status	Published - 10 Aug 2020

Bibliographical note

© The Royal Society of Chemistry 2020. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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10.1039/D0RE00174K

10 Direct comparison of safer or sustainable alternative dipolar aprotic solvents for use in coupling reactions
© The Royal Society of Chemistry 2020. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.
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Cite this

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title = "Direct comparison of safer or sustainable alternative dipolar aprotic solvents for use in carbon–carbon bond formation",

abstract = "There is a lot of interest in the development of new, safer and more sustainable polar aprotic solvents due to their importance in industrial applications and significant safety issues with the most commonly used examples. One such area of application is in pharmaceutically relevant C–C coupling reactions, where polar aprotic solvents are commonly used for solubility and to stabilise reaction intermediates. Although there are now a number of excellent alternatives in the literature, to date they have not been compared in a single study. This study demonstrates the effectiveness of the green solvents N-butylpyrrolidinone (NBP), γ-valerolactone (GVL), propylene carbonate (PC) and dihydrolevoglucosenone (Cyrene) in Heck and Baylis–Hillman reactions. Good conversions and initial rates were observed in GVL and NBP in Heck reactions. Cyrene exhibited high initial rates of reaction and high yields in the Baylis–Hillman reaction. This demonstrates Cyrene to be a promising alternative polar aprotic solvent for this reaction.",

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AU - McElroy, Rob

AU - Hunt, Andrew

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