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Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

Authors :
Raju Vaggu
Nagender Thadem
Manda Rajesh
René Grée
Saibal Das
CSIR Indian Institute of Chemical Technology (IICT)
Université de Rennes (UR)
Institut des Sciences Chimiques de Rennes (ISCR)
Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes)
Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
V.R. and N.T. thank CSIR for their fellowships. M.R. thanks CSIR-IICT for financial support. R.G. and S.D. thanks the Indo-French 'Joint Laboratory for Natural Products and Synthesis toward Affordable Health' program between CSIR- Indian Institute of Chemical Technology and University of Rennes for the platform to carry out the finding jointly. We sincerely thank the Department of Analytical and Structural Chemistry at CSIR-IICT for all the analytical support and especially Dr. Sridhar Balasubramanian for X-ray crystal data. We gratefully acknowledge the overall support by CSIR-IICT to perform the research (IICT/Pubs./2023/011).
Source :
Organic Letters, Organic Letters, 2023, 25 (15), pp.2594-2599. ⟨10.1021/acs.orglett.3c00487⟩
Publication Year :
2023
Publisher :
American Chemical Society (ACS), 2023.

Abstract

International audience; We herein demonstrate the acylsilane-directed Rh-catalyzed arene C-H bond alkylation with maleimides. The resulting derivatives were utilized in visible-light-induced intramolecular siloxycarbene-amide cyclization for the synthesis of new tricyclic γ-lactams. In parallel, we also harnessed the same acylsilane and maleimide units through [3 + 2] carbo-annulation by using Ru-catalysis. A wide range of maleimides and aroylsilanes were used to establish the broadness of these transformations.

Details

ISSN :
15237052 and 15237060
Volume :
25
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....06ed83196d720b71f51cfb12963b0a7d