Scalable and Sustainable Reductive Amidation of Nitroarenes, Nitroalkenes, and Nitroalkyls with Acyl Saccharins in Aqueous Media DOI Creative Commons

Deákné Re,

Sunil L. Khamkar,

R. Mohan

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Abstract We present a scalable and sustainable methodology for synthesizing N-substituted amides directly from readily available nitroarenes, nitroalkenes, nitroalkyls, acyl saccharin in aqueous media. This eco-friendly atom-efficient approach, which avoids column chromatography, demonstrates excellent functional group compatibility high yield key amide structures. The method's applicability extends to the formal synthesis of Disyprin, bromopyrrole alkaloid, as well amide-based pharmaceuticals agrochemicals. Additionally, we demonstrate its effectiveness multigram-scale paracetamol, alongside solvent recycling. A comprehensive Life Cycle Assessment (LCA; ISO 14044) was conducted evaluate environmental impacts sustainability nine selected Active Pharmaceutical Ingredients (APIs) produced via Non-Amidation Route (NAR) Amidation (AR). study reveals that saccharin-acetylation methods significantly reduce carbon footprints compared NAR is notably carbon-negative resource-efficient. Further impact reduction achievable through recycling adoption low-carbon renewable energy sources, highlighting potential saccharin-based processes substantially mitigate burdens pharmaceutical synthesis.

Язык: Английский

Acyl Iodide Synthesis from Carboxylic Acids Using a Novel Ph2P(O)H‐I2 Binary System and Its Application to Facile Preparation of Amides, Esters, and Thioesters DOI

Kohsuke Fujiwara,

Shinichi Kawaguchi, Yuki Yamamoto

и другие.

ChemistrySelect, Год журнала: 2024, Номер 9(39)

Опубликована: Окт. 1, 2024

Abstract Acyl iodides are expected to be excellent acylating agents due the low bond dissociation energy of carbon–iodine and high capability iodine as a leaving group. Unfortunately, preparative methods for acyl directly from carboxylic acids rather limited. In this work, we found that novel binary system combining I 2 diphenylphosphine oxide (Ph P(O)H) provides simple method preparation acids. Furthermore, subsequent one‐pot reaction with appropriate nucleophiles, such amines, alcohols, thiols, afforded corresponding amides, esters, thioesters, respectively, in good yields.

Язык: Английский

Процитировано

0
Scalable and Sustainable Reductive Amidation of Nitroarenes, Nitroalkenes, and Nitroalkyls with Acyl Saccharins in Aqueous Media DOI Creative Commons

Deákné Re,

Sunil L. Khamkar,

R. Mohan

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Abstract We present a scalable and sustainable methodology for synthesizing N-substituted amides directly from readily available nitroarenes, nitroalkenes, nitroalkyls, acyl saccharin in aqueous media. This eco-friendly atom-efficient approach, which avoids column chromatography, demonstrates excellent functional group compatibility high yield key amide structures. The method's applicability extends to the formal synthesis of Disyprin, bromopyrrole alkaloid, as well amide-based pharmaceuticals agrochemicals. Additionally, we demonstrate its effectiveness multigram-scale paracetamol, alongside solvent recycling. A comprehensive Life Cycle Assessment (LCA; ISO 14044) was conducted evaluate environmental impacts sustainability nine selected Active Pharmaceutical Ingredients (APIs) produced via Non-Amidation Route (NAR) Amidation (AR). study reveals that saccharin-acetylation methods significantly reduce carbon footprints compared NAR is notably carbon-negative resource-efficient. Further impact reduction achievable through recycling adoption low-carbon renewable energy sources, highlighting potential saccharin-based processes substantially mitigate burdens pharmaceutical synthesis.

Язык: Английский

Процитировано

0