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N -acyl DBN tetraphenylborate salts as N -acylating agents


Reference:

Taylor, J. E., Jones, M. D., Williams, J. M. J. and Bull, S. D., 2012. N -acyl DBN tetraphenylborate salts as N -acylating agents. Journal of Organic Chemistry, 77 (6), pp. 2808-2818.

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Official URL:

http://dx.doi.org/10.1021/jo202647f

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.

Details

Item Type Articles
CreatorsTaylor, J. E., Jones, M. D., Williams, J. M. J. and Bull, S. D.
DOI10.1021/jo202647f
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code29336

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