Abstract:
Treatment of nonanamides C8H17C(O)NR2 (R = H or Et) with superelectrophilic complex CBr4·2AlBr3 under CO atmosphere followed by quenching with nucleophiles NuH cleanly gives 7-methyl-7-(Nu-carbonyl)octanamide bifunctional derivatives.
Citation:
I. S. Akhrem, L. V. Afanas'eva, I. M. Churilova, O. I. Artyushin, N. D. Kagramanov, “Chemo- and regioselective remote functionalization of nonanamides via sp3 C–H bond cleavage under superelectrophilic conditions”, Mendeleev Commun., 25:2 (2015), 124–125
Linking options:
https://www.mathnet.ru/eng/mendc2321
https://www.mathnet.ru/eng/mendc/v25/i2/p124
This publication is cited in the following 5 articles:
Ritika Sharma, Upendra Sharma, “Remote C-H bond activation/transformations: A continuous growing synthetic tool; Part II”, Catalysis Reviews, 60:4 (2018), 497
I. S. Akhrem, D. V. Avetisyan, L. V. Afanas'eva, A. A. Tyutyunov, O. I. Artyushin, N. D. Kagramanov, “Regioselective functionalization of gem-bis(trifluoromethylated) alkanols”, Mendeleev Commun., 28:6 (2018), 651–652
Yurii A. Borisov, Irena S. Akhrem, “DFT mechanistic study of reactions of S6H6 and 1,3,5-Ad3C6H3 with CBr3. The first example of hydride transfer from aromatic C H bond to electrophile”, Journal of Molecular Catalysis A: Chemical, 426 (2017), 610
Irena S. Akhrem, Dzhul'etta V. Avetisyan, Lyudmila V. Afanas'eva, Oleg I. Artyushin, Nikolai D. Kagramanov, Andrey L. Sigan, “A new method of one-pot synthesis of dicarboxylic acid derivatives and diketones containing quaternary carbon atom and remote functional groups from linear acyl halides”, Tetrahedron Letters, 58:42 (2017), 4014
Irena S. Akhrem, Djul'etta V. Avetisyan, Lyudmila V. Afanas'eva, Oleg I. Artushin, Nikolai D. Kagramanov, “Superelectrophilic sp 3 C H bond intermolecular functionalization of primary alcohols C n H 2 n +1 OH ( n = 7, 8, 9) leading to new neo-alcohols with remote functional groups or new macrocyclic lactides”, Tetrahedron Letters, 57:17 (2016), 1863
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