Peer-reviewedCC BYOrganic letters
Rh(III)-Catalyzed [4 + 2] Spiroannulation of 2-Phenylbenzimidazoles with Isomerizable 3-Methylmaleimides: Synthesis of Spiro-Fused Benzimidazoisoquinoline Succinimides.
- 1Department of Applied Chemistry, Laboratory of Combinatorial Drug Design, National Yang-Ming Chiao-Tung University, Hsinchu300-10, Taiwan.
- 2Department of Chemistry, MES Abasaheb Garware College, Pune411004, Maharashtra, India.
- 3Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung807-08, Taiwan.
Abstract
A Rh(III)-catalyzed exclusive [4 + 2] cascade cyclization of 2-phenylbenzimidazoles with 3-methylmaleimides for the synthesis of spiro-fused benzimidazoisoquinoline succinimides via C-H activation is reported. The detailed mechanistic study revealed that the reaction proceeds through N-directed C-H activation of 2-phenylbenzimidazole. Subsequent migratory insertion of the rhodium-mediated formation of isomeric maleimide into the Rh-C bond and reductive elimination affords the polycyclic spiro-fused benzimidazoisoquinoline succinimide.
BibTeX
@article{chiu2026rhiiicatalyzed,
title = {{Rh(III)-Catalyzed [4 + 2] Spiroannulation of 2-Phenylbenzimidazoles with Isomerizable 3-Methylmaleimides: Synthesis of Spiro-Fused Benzimidazoisoquinoline Succinimides.}},
author = {Wei-Jung Chiu and Meng-Han Shih and Indrajeet J Barve and Chung-Ming Sun},
journal = {Organic letters},
year = {2026},
month = oct,
doi = {10.1021/acs.orglett.6c03335},
url = {https://europepmc.org/article/MED/42917809},
note = {CC BY},
}
RIS
TY - JOUR
TI - Rh(III)-Catalyzed [4 + 2] Spiroannulation of 2-Phenylbenzimidazoles with Isomerizable 3-Methylmaleimides: Synthesis of Spiro-Fused Benzimidazoisoquinoline Succinimides.
AU - Wei-Jung Chiu
AU - Meng-Han Shih
AU - Indrajeet J Barve
AU - Chung-Ming Sun
PY - 2026
DA - 2026/10/01
JO - Organic letters
DO - 10.1021/acs.orglett.6c03335
UR - https://europepmc.org/article/MED/42917809
AB - A Rh(III)-catalyzed exclusive [4 + 2] cascade cyclization of 2-phenylbenzimidazoles with 3-methylmaleimides for the synthesis of spiro-fused benzimidazoisoquinoline succinimides via C-H activation is reported. The detailed mechanistic study revealed that the reaction proceeds through N-directed C-H activation of 2-phenylbenzimidazole. Subsequent migratory insertion of the rhodium-mediated formation of isomeric maleimide into the Rh-C bond and reductive elimination affords the polycyclic spiro-fused benzimidazoisoquinoline succinimide.
SN - 1523-7060
SN - 1523-7052
ER -