{"title":"Dehydrative Coupling of Carboxylic Acids with Amines in the Presence of Sodium Azepane-1-carbodithioate","authors":"Ayhan Yıldırım","doi":"10.1021/acs.oprd.6c00193","DOIUrl":null,"url":null,"abstract":"<p>The reaction of a carboxylic acid with an amine in the\r\npresence\r\nof a catalytic carbodithioate affords the corresponding amide under\r\nthermal conditions, excluding the requirement for stoichiometric coupling\r\nreagents. The high-yield preparation of amides in the presence of\r\nsodium azepane-1-carbodithioate, which can be readily prepared, demonstrates\r\nthat this agent does not behave as a simple nucleophile but rather\r\nplays a critical role in acyl activation and transfer. The advantages\r\nof the developed simple catalytic method include minimization of reagents,\r\nthe ability to operate in a solvent-free environment in many cases,\r\nminimal solvent requirement, high product yield, and applicability\r\nfor scale-up in the synthesis of amides. This method allows for the\r\nsuccessful use of various aliphatic and/or aromatic substrates as\r\nwell as some functionalized carboxylic acids. The study also provided\r\nmechanistic insights into the amidation process through Fourier transform\r\ninfrared analysis and density functional theory calculations.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"30 8","pages":"2323–2338"},"PeriodicalIF":3.3000,"publicationDate":"2026-08-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Process Research & Development","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.oprd.6c00193","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/7/17 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
The reaction of a carboxylic acid with an amine in the
presence
of a catalytic carbodithioate affords the corresponding amide under
thermal conditions, excluding the requirement for stoichiometric coupling
reagents. The high-yield preparation of amides in the presence of
sodium azepane-1-carbodithioate, which can be readily prepared, demonstrates
that this agent does not behave as a simple nucleophile but rather
plays a critical role in acyl activation and transfer. The advantages
of the developed simple catalytic method include minimization of reagents,
the ability to operate in a solvent-free environment in many cases,
minimal solvent requirement, high product yield, and applicability
for scale-up in the synthesis of amides. This method allows for the
successful use of various aliphatic and/or aromatic substrates as
well as some functionalized carboxylic acids. The study also provided
mechanistic insights into the amidation process through Fourier transform
infrared analysis and density functional theory calculations.
期刊介绍：
The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.
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