Peer-reviewedCC BY-NC-ND 4.0Organic Letters
Functionalization of the 1,8-Naphthalimide Core with Weak Nucleophiles
Abstract
A new synthetic strategy for the functionalization of the 1,8-naphthalimide core with weak nucleophiles was developed and is presented herein. By selection of the appropriate base and reaction temperature, access to difluoro, dialkoxy (including with a fused dioxa ring), and mixed fluoro-alkoky and alkoxy-hydroxy derivatives was achieved. All of the reactions proceed rapidly on a gram scale, affording the target products in a high yield (80–97%) and purity from inexpensive, commercially available starting compounds and reagents.
Related
- Oxygen-enabled Fe-catalyzed heteroatom α-C(sp3)–H functionalization with nucleophiles
- Unlocking Catalyst Activation as a Critical Bottleneck in Cross‐Coupling Reactions: Room‐Temperature Couplings of Weak Nucleophiles Enabled by [Pd(1‐MeNAP)TFA] 2 Precatalysts
- Functionalization of strong C(sp3)–H bonds in the presence of weak C(sp3)–H bonds enables the block-selective modification of thermoplastic elastomers
- Anions as catalysts: from organosilanes as pro-nucleophiles to base-embedding electrophiles.
- Reactivity of Ambident Nucleophiles in Magnetic Fields: a Combined Conceptual DFT and Current-DFT Study
BibTeX
@article{mutovska2026functionalization,
title = {{Functionalization of the 1,8-Naphthalimide Core with Weak Nucleophiles}},
author = {Monika Mutovska and Konstantin Konstantinov and Irena Zagranyarska and Darío Puchán Sánchez and Magali Allain and Arthur David and Silvia Angelova and Stanimir Stoyanov and Clément Cabanetos and Yulian Zagranyarski},
journal = {Organic Letters},
year = {2026},
month = oct,
doi = {10.1021/acs.orglett.5c05282},
url = {https://hal.science/hal-05698602v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Functionalization of the 1,8-Naphthalimide Core with Weak Nucleophiles
AU - Monika Mutovska
AU - Konstantin Konstantinov
AU - Irena Zagranyarska
AU - Darío Puchán Sánchez
AU - Magali Allain
AU - Arthur David
AU - Silvia Angelova
AU - Stanimir Stoyanov
AU - Clément Cabanetos
AU - Yulian Zagranyarski
PY - 2026
DA - 2026/10/08
JO - Organic Letters
DO - 10.1021/acs.orglett.5c05282
UR - https://hal.science/hal-05698602v1
AB - A new synthetic strategy for the functionalization of the 1,8-naphthalimide core with weak nucleophiles was developed and is presented herein. By selection of the appropriate base and reaction temperature, access to difluoro, dialkoxy (including with a fused dioxa ring), and mixed fluoro-alkoky and alkoxy-hydroxy derivatives was achieved. All of the reactions proceed rapidly on a gram scale, affording the target products in a high yield (80–97%) and purity from inexpensive, commercially available starting compounds and reagents.
SN - 1523-7060
SN - 1523-7052
ER -