Rhodium(<scp>ii</scp>) catalysed highly diastereoselective synthesis of indolyl-pyrrolo[2,1-<i>a</i>]isoindoles from phthalimide-derived <i>N</i>-sulfonyl-1,2,3-triazoles and indoles
A synthetic method has been developed for the diastereoselective domino synthesis of indolyl-pyrrolo[2,1-<i>a</i>]isoindoles from phthalimide-derived <i>N</i>-sulfonyl-1,2,3-triazoles and indoles. The reaction proceeds <i>via</i> ring chain isomerization of triazoles to give α-imino diazo compounds. Then, denitrogenative generation of α-imino Rh(II) carbenes followed by intramolecular oxygen insertion and nucleophilic addition of indoles delivers the indolyl-pyrrolo[2,1-<i>a</i>]isoindoles. The synthetic utility of the products was also demonstrated through selective Grignard reagent addition and NaBH<sub>4</sub> reduction reactions.
Authors
- Swapnil Patil (ORCID: https://orcid.org/0000-0002-0950-549X)
- Sudam Ganpat Dawande (ORCID: https://orcid.org/0000-0003-1632-1434)
- Bhalchandra Mahadeo Bhanage (ORCID: https://orcid.org/0000-0001-9538-3339)
- Ajay Verma (ORCID: https://orcid.org/0000-0002-0772-105X)
Institutions
- Institute of Chemical Technology (IN)
- University of Allahabad (IN)
- Indian Institute of Technology Madras (IN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob01295c
- Citations
- 1
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.94