N-acyl DBN tetraphenylborate salts as N-acylating agents

The Journal of Organic Chemistry
James E TaylorSteven D Bull

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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Citations

May 16, 2013·The Journal of Organic Chemistry·Sachitanand M MaliHosahudya N Gopi
Nov 2, 2014·Organic & Biomolecular Chemistry·Erik Daa FunderKurt V Gothelf
Oct 8, 2016·Organic & Biomolecular Chemistry·Caroline S JonesJonathan M J Williams
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Jun 3, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tarek S IbrahimMohamed Elagawany
Feb 3, 2018·Organic & Biomolecular Chemistry·Yongmei LiuMichal Szostak
Aug 1, 2021·Chemistry, an Asian Journal·Chandrasekaran Sivaraj, Thirumanavelan Gandhi

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