Journal
CHEMICAL SCIENCE
Volume 11, Issue 39, Pages 10770-10777Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc01373k
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Funding
- SERB-India [EMR/2014/385]
- CSIR, India
- CNRS
- Ecole Polytechnique [ANR-18-CE07-0012-02]
- UPSaclay
- Agence Nationale de la Recherche (ANR) [ANR-18-CE07-0012] Funding Source: Agence Nationale de la Recherche (ANR)
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Direct difunctionalization of chemically distinctortho- andperi-C-H bonds of fused hetero(arenes) is illustrated through an unusual one-pot domino {[4 + 2] & [5 + 2]} double annulation with alkynes for the first time. This process is viable under Ru(ii)-catalysis using a sulfoximine directing group and builds four bonds [(C-C)-(C-N) and (C-C)-(C-O)] in a single operation. Such synthetic manifestation offers access to uncommon [6,7]-fused oxepino-pyridine skeletons. DFT calculations provide mechanistic insight into this double annulation of naphthoic acid derivatives with alkynes and corroborate the participation of a ruthena-oxabicyclooctene intermediate, which is responsible for the rare 7-membered ring formation.
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