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

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 elimina...

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Published inEuropean journal of organic chemistry Vol. 27; no. 41
Main Authors Hwu, Jih Ru, Gupta, Nitesh K., Panja, Avijit, Chang, Chin‐Hwa, Huang, Wen‐Chieh, Tsai, Yu‐Ran, Chung, Kau‐Shu, Tan, Kui‐Thong, Lin, Chun‐Cheng, Hwang, Kuo‐Chu, Tsay, Shwu‐Chen
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 04.11.2024
Wiley Subscription Services, Inc
Subjects
Acetonitrile
Bond formation
Cascade chemical reactions
Cesium fluorides
Chemical bonds
Chemical synthesis
Chemistry
Chemistry, Organic
Domino reaction
E factor
Imines
Neat
Nitriles
Physical Sciences
Productivity
Reagents
Science & Technology
Solvents
Volume productivity
ORGANIC-SYNTHESIS
COUNTERATTACK REAGENTS
Bond formation
E factor
ARYNES
Neat
Domino reaction
AMINO-ACID
COOPERATIVE CATALYSIS
SOLVENT-FREE
GREEN CHEMISTRY
ACETONITRILE
EFFICIENT
DERIVATIVES
Volume productivity
Online AccessGet full text
ISSN1434-193X
1099-0690
DOI10.1002/ejoc.202400658

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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. This newly developed single‐flask, solvent‐free process accomplishes sequential C−N and C−C bond formations. It leads to (β‐cyano)anilines by use of aryl triflates, Schiff bases, and CH3CN as a reagent. Key features of this neat method include a domino process, ambient temperature, short reaction time, and alignment with sustainability principles.
AbstractList 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 (CH 3 CN) in a 1 : 1 : 1 ratio, among which CH 3 CN 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.
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. This newly developed single‐flask, solvent‐free process accomplishes sequential C−N and C−C bond formations. It leads to (β‐cyano)anilines by use of aryl triflates, Schiff bases, and CH3CN as a reagent. Key features of this neat method include a domino process, ambient temperature, short reaction time, and alignment with sustainability principles.
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.
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 (beta-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 degrees C for 1.0 h to give (beta-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.
Author Hwu, Jih Ru
Tsay, Shwu‐Chen
Huang, Wen‐Chieh
Lin, Chun‐Cheng
Gupta, Nitesh K.
Panja, Avijit
Hwang, Kuo‐Chu
Chang, Chin‐Hwa
Tsai, Yu‐Ran
Chung, Kau‐Shu
Tan, Kui‐Thong
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  organization: National Tsing Hua University
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  givenname: Nitesh K.
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  organization: National Tsing Hua University
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  organization: National Tsing Hua University
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  surname: Tsay
  fullname: Tsay, Shwu‐Chen
  organization: National Tsing Hua University
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Issue 41
Keywords ORGANIC-SYNTHESIS
COUNTERATTACK REAGENTS
Bond formation
E factor
ARYNES
Neat
Domino reaction
AMINO-ACID
COOPERATIVE CATALYSIS
SOLVENT-FREE
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DERIVATIVES
Volume productivity
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Gan C. (e_1_2_10_13_1) 2006; 3
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e_1_2_10_42_2
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e_1_2_10_72_1
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e_1_2_10_35_2
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e_1_2_10_9_1
e_1_2_10_59_1
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Snippet 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....
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SubjectTerms Acetonitrile
Bond formation
Cascade chemical reactions
Cesium fluorides
Chemical bonds
Chemical synthesis
Chemistry
Chemistry, Organic
Domino reaction
E factor
Imines
Neat
Nitriles
Physical Sciences
Productivity
Reagents
Science & Technology
Solvents
Volume productivity
Title Sustainable Domino C−N/C−C Bond Formation with Outstanding E Factors and High Volume Productivity
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.202400658
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Volume 27
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