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Synthesis of silyl indenes by ruthenium-catalyzed aldehyde- and acylsilane-enabled C-H alkylation/cyclization.
Org Biomol Chem
January 2024
College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121 Zhejiang, China.
A ruthenium-catalyzed C-H alkylation/cyclization sequence is presented to prepare silyl indenes with atom and step-economy. This domino reaction is triggered by acyl silane-directed C-H activation, and an aldehyde controlled the following enol cyclization/condensation other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyl indenes allows access to a diverse range of interesting indene and indanone derivatives.
View Article and Find Full Text PDFRuthenium-Catalyzed Remote Difunctionalization of Nonactivated Alkenes for Double meta-C(sp )-H/C-6(sp )-H Functionalization.
Angew Chem Int Ed Engl
June 2023
Institut für Organische und Biomolekulare Chemie and Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität, Tammannstraße 2, 37077, Göttingen, Germany.
Twofold distal C-H functionalization was accomplished by difunctionalization of nonactivated alkenes to provide rapid access to multifunctionalized molecules. The multicomponent ruthenium-catalyzed remote 1,n-difunctionalization (n=6,7) of nonactivated alkenes with fluoroalkyl halides and heteroarenes in a modular manner is reported. The meta-C(sp )-H/C-6(sp )-H distal functionalization featured mild conditions, unique selectivity, and broad substrate scope with a domino process for twofold remote C(sp )-H/C(sp )-H activation of the sequential formation of three different carbon-centered radicals.
View Article and Find Full Text PDFRuthenium-Catalyzed Brook Rearrangement Involved Domino Sequence Enabled by Acylsilane-Aldehyde Corporation.
Org Lett
July 2020
College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China.
A ruthenium-catalyzed [1,2]-Brook rearrangement involved domino sequence is presented to prepare highly functionalized silyloxy indenes with atomic- and step-economy. This domino reaction is triggered by acylsilane-directed C-H activation, and the aldehyde controlled the subsequent enol cyclization/Brook Rearrangement other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyloxy indenes allows access to a diverse range of interesting indene and indanone derivatives.
View Article and Find Full Text PDFTraceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines.
Org Lett
May 2017
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462066, MP, India.
A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.
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