Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent

Vega‐Hernández, Karen de la; Senatore, Raffaele; Miele, Margherita; Urban, Ernst; Hölzer, W.; Pace, Vittorio

doi:10.1039/c8ob02312c

Cited by 30 publications

(17 citation statements)

References 95 publications

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“…11d , 12 Taking a step forward towards developing sustainable, mechanistically well-supported aerobic polar organometallic chemistry, here we report our findings on the mechanism and application of lithium-mediated amidation and transamidation reactions of ethyl esters and an N -Boc-substituted benzamide in air using the biomass derived solvents glycerol and 2-methyltetrahydrofuran (2-MeTHF, Scheme 1 ). 13 , 14 …”

Section: Introductionmentioning

confidence: 99%

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents

et al. 2020

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Section: Introductionmentioning

confidence: 99%

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents

et al. 2020

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“… 352 CPME is now included in the guidance as of 2020/21. 353 Therefore, it is imperative that regulatory updates and guidance are carried out in a time frame that supports the rapidly progressing developments in greener, more sustainable processes.…”

Section: Future Directions For Development Of More Sustainable Solven...mentioning

confidence: 99%

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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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.

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“…Alkanoyl chlorides such as myristoyl chloride was completely unreactive. Their NMR experiments suggested the existence of a possible silyl ether intermediate (79), which was generated by direct hydrosilylation of acyl chloride and subsequently collapsed to an aldehyde in time spontaneously or by various workups.…”

Section: Reduction Of Acyl Halidesmentioning

confidence: 99%

Partial reductions of carboxylic acids and their derivatives to aldehydes

Yang

2022

Org. Chem. Front.

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Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent

Abstract: Thioformamides are easily prepared – under full chemocontrol – through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent.

Cited by 30 publications

References 95 publications

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Partial reductions of carboxylic acids and their derivatives to aldehydes

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