1363906-80-2Relevant articles and documents
N -acyl DBN tetraphenylborate salts as N -acylating agents
Taylor, James E.,Jones, Matthew D.,Williams, Jonathan M. J.,Bull, Steven D.
experimental part, p. 2808 - 2818 (2012/04/23)
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.
N-acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents
Taylor, James E.,Williams, Jonathan M.J.,Bull, Steven D.
experimental part, p. 4074 - 4076 (2012/08/28)
Air-stable and crystalline N-acyl DBN tetraphenylborate salts have been shown to be effective O-acylating agents, reacting with both primary and secondary alcohols to give the corresponding esters in good yields. In the case of diols, the N-acyl DBN·BPh4 salts have been shown to acylate regioselectively the primary alcohol functionality in the presence of a secondary alcohol. The DBN hydrotetraphenylborate side product can be readily removed by filtration, providing the ester products without the need for further purification.
