Using NBS Entirely: One-Pot Tandem Synthesis of <i>N</i>-Arylsuccinimides from Activated Arenes under Microwave Irradiation

Higa, Vanessa M.; Omori, Alvaro T.

doi:10.21577/0103-5053.20260053

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Sumário

Communication • J. Braz. Chem. Soc. 37 • 2026 • https://doi.org/10.21577/0103-5053.20260053 linkcopy

Using NBS Entirely: One-Pot Tandem Synthesis of N-Arylsuccinimides from Activated Arenes under Microwave Irradiation

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

N-Bromosuccinimide (NBS) is a versatile brominating reagent. It is used not only in radical bromination but also in electrophilic addition and electrophilic substitution reactions. NBS can be used to obtain aryl bromides, which are useful for further functionalization, such as coupling reactions for C/N/O/S-aryl bond formation. However, the succinimide group of NBS is poorly explored and is often treated as a waste. In this work, it is proposed the full use of NBS, both for bromination of arenes and for the incorporation of the succinimide group in a one-pot fashion. Using low-cost reagents such as Cu₂O and K₃PO₄, N-arylsuccinimides were obtained in moderate to good yields directly from non-halogenated aromatics. It was observed that microwave irradiation was crucial to circumvent the low nucleophilicity of succinimide.

Keywords:
N-arylsuccinimides; Ullmann reaction; imidation; NBS


Exp	1a / (mol L^-1)	NBS / (mol L^-1)	Copper source	Additivea	Heating conditions	2ab / %
1	2	2	Cu (3 eq.)	-	reflux, 12 h	6
2	1	1	Cu (6 eq.)	-	microwaves, 140 ºC, 3 × 10 min	19
3	1	1	Cu₂O (0.5 eq.)	-	microwaves, 150 ºC, 3 × 10 min	21
4	1	1	Cu₂O (0.2 eq.)	-	microwaves, 150 ºC, 3 × 10 min	16
5	1	1	Cu₂O (0.7 eq.)	K₃PO₄	microwaves, 170 ºC, 3 × 10 min	35
6	1	1	Cu₂O (0.7 eq.)	Cs₂CO₃	microwaves, 150 ºC, 3 × 10 min	30
7	1	1	Cu₂O (0.7 eq.)	K₂CO₃	microwaves, 150 ºC, 3 × 10 min	15
8c	1	1	Cu₂O (0.7 eq.)	Cs₂CO₃	microwaves, 90 ºC, 3 × 10 min	-

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[TFN1] ^a
0.5 equiv.

[TFN2] ^b
Isolated yield.

[TFN3] ^c
Acetonitrile as solvent.