AI Article Synopsis
- Air-stable and crystalline N-acyl DBN tetraphenylborate salts were created using DBN and acyl chlorides with sodium tetraphenylborate.
- These salts serve as efficient N-acylating agents, successfully reacting with various amines and sulfonamides to yield N-acylated products in good quantities.
- The process allows for easy purification as the byproduct can be filtered out, and these salts offer advantages over acyl halides, including stability in air, no free acid production, and suitability for higher temperature conditions.
Article Abstract
Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been synthesized from 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) and the corresponding acyl chloride in the presence of sodium tetraphenylborate. The salts have been shown to be effective N-acylating agents, reacting with primary amines, secondary amines, and sulfonamides to form the corresponding N-acylated products in good yields. The DBN hydrotetraphenylborate byproduct can be conveniently removed by filtration, providing pure N-acylated products without the need for further purification. The N-acyl DBN tetraphenylborate salts are attractive alternatives to acyl halides as they can be stored in air without decomposition, avoid the production of free acid during acylation reactions, and can be used under more forcing thermal conditions.
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| http://dx.doi.org/10.1021/jo202647f | DOI Listing |
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