Dipolar aprotic and ethereal solvents
comprise just over 40% of
all organic solvents utilized in synthetic organic, medicinal, and
process chemistry. Unfortunately, many of the common “go-to”
solvents are considered to be “less-preferable” for
a number of environmental, health, and safety (EHS) reasons such as
toxicity, mutagenicity, carcinogenicity, or for practical handling
reasons such as flammability and volatility. Recent legislative changes
have initiated the implementation of restrictions on the use of many
of the commonly employed dipolar aprotic solvents such as dimethylformamide
(DMF) and
N
-methyl-2-pyrrolidinone (NMP), and for
ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and
societal pressures, the need to identify and implement the use of
alternative solvents that are greener, safer, and more sustainable
has never been greater. Within this review, the ubiquitous nature
of dipolar aprotic and ethereal solvents is discussed with respect
to the physicochemical properties that have made them so appealing
to synthetic chemists. An overview of the current legislative restrictions
being imposed on the use of dipolar aprotic and ethereal solvents
is discussed. A variety of alternative, safer, and more sustainable
solvents that have garnered attention over the past decade are then
examined, and case studies and examples where less-preferable solvents
have been successfully replaced with a safer and more sustainable
alternative are highlighted. Finally, a general overview and guidance
for solvent selection and replacement are included in the Supporting
Information of this review.
A mechanistic study into the copper(I)-catalysed sulfonylative Suzuki-Miyaura reaction, incorporating sulfur dioxide, is described. Utilising spectroscopic and computational techniques, an exploration into the individual components of the competing catalytic cycles...
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