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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Selective C-N Bond Cleavage of N-Acylisatins: Towards High Performance Acylation/Arylation/Transamination Reagents》. Authors are Xiong, Li; Deng, Rong; Liu, Tingting; Luo, Zhongfeng; Wang, Zijia; Zhu, Xiao-Feng; Wang, Hui; Zeng, Zhuo.The article about the compound:Tricyclohexylphosphonium tetrafluoroboratecas:58656-04-5,SMILESS:F[B-](F)(F)F.[PH+](C1CCCCC1)(C2CCCCC2)C3CCCCC3).Quality Control of Tricyclohexylphosphonium tetrafluoroborate. Through the article, more information about this compound (cas:58656-04-5) is conveyed.
New multipurpose arylation/acylation/transamination reagents, N-acylisatins, I (R = Ph, Me, furan-2-yl, cyclohexyl, etc.) have been developed by selective ‘inside-outside’ C-N bond cleavage under different catalytic conditions. As activated amides, N-acylisatins I undergo Rh-catalyzed C-H arylation and Pd-catalyzed acylation by cleavage outside the C-N bond, and the desired biaryls RR1 (R1 = benzo[h]quinolin-10-yl, 5-methyl-1-(pyrimidin-2-yl)-1H-indol-2-yl, 3-methyl-1-(pyrimidin-2-yl)-1H-indol-2-yl, etc.) and diaryl ketones R2C6H4C(O)C6H5 (R2 = H, 4-Me, 3-OMe, 4-F, etc.) were obtained in good to excellent yields. Generally, the combination of N-acylisatins I (R = Ph, (A)) with amines such as N-methylaniline, 2-methylpropan-2-amine, aniline leads to a ring-opening reaction and formation of transamination products 2-(PhC(O)NH)C6H4C(O)C(O)NR3R4 (R3 = H, Me; R4 = Ph, t-Bu) in a predictable manner through inside C-N bond cleavage. Interestingly, treatment of N-acylisatins (A) with amines lead to unexpected outer-ring transamination products PhC(O)NR3R4 when CsF is added, which shows that CsF can favor the outside C-N bond cleavage path. Notably, this work presents a new strategy for multiple chem. transformations of a single amide to achieve various products by selective C-N bond cleavage.
This literature about this compound(58656-04-5)Quality Control of Tricyclohexylphosphonium tetrafluoroboratehas given us a lot of inspiration, and I hope that the research on this compound(Tricyclohexylphosphonium tetrafluoroborate) can be further advanced. Maybe we can get more compounds in a similar way.
Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem