Sustainable Domino C−N/C−C Bond Formation with Outstanding E Factors and High Volume Productivity

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Abstract
One of the primary concerns in the development of new chemical reactions pertains to the choice of solvents, many of which can have harmful ecological impacts. Additionally, a major portion of waste generated in the chemical and pharmaceutical industries comes from the solvents employed. The elimination of solvent usage is highly desirable for creation of environmentally friendly chemical processes as it leads to a substantial reduction in waste production. Accordingly, a novel neat reaction was developed for the synthesis of (β‐amino)nitriles as a prominent moiety through a domino process. It involved the use of silylphenyl triflates, Schiff bases, and acetonitrile (CH3CN) in a 1 : 1 : 1 ratio, among which CH3CN served as a starting material rather than a solvent. This reaction was initiated by caesium fluoride (CsF) to form an aryne through 1,2‐elimination followed by sequential 1,2‐addition, proton transfer, and a second 1,2‐addition. Complete conversion was carried out at 25 °C for 1.0 h to give (β‐amino)nitriles in 76–88 % yields. This solvent‐free reaction minimized waste production and reduced costs associated with extra reagents, solvents, and labour. It possesses a compelling E factor and impressive volume productivity. This reaction sets a new benchmark for solvent‐free aryne domino processes in green chemistry advancements.
Funding Information
  • National Science and Technology Council (112-2113-M-007-001, 111-2634-F-007-023)
  • Ministry of Higher Education and Scientific Research (111QR001I5, 110QR001I5)
  • National Tsing Hua University (112QI055E1)

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