Iqbal, Saqib A. published the artcileAcyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3, Recommanded Product: N-(4-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pivalamide, the publication is Angewandte Chemie, International Edition (2019), 58(43), 15381-15385, database is CAplus and MEDLINE.
Indoles are privileged heterocycles found in many biol. active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C-H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-Amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C-H borylation enabling selective formation of C5-BPin-indoles.
Angewandte Chemie, International Edition published new progress about 2246585-66-8. 2246585-66-8 belongs to amides-buliding-blocks, auxiliary class Boronic acid and ester, name is N-(4-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pivalamide, and the molecular formula is C18H28BNO3, Recommanded Product: N-(4-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pivalamide.
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