Journal ArticleDOI
N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed α-Arylation of Oxindoles with Aryl Chlorides and Aerobic Oxidation of the Products in a One-Pot Procedure
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TLDR
NHC-Pd(II)-Im complex 1 was found to be an effective catalyst for the α-arylation of unprotected oxindoles with aryl chlorides to give products 4 in 44-98% yields under a N2 atmosphere.About:
This article is published in Organic Letters.The article was published on 2013-03-01. It has received 52 citations till now. The article focuses on the topics: Aryl & Palladium.read more
Citations
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Journal ArticleDOI
Direct C-H bond arylation of (benzo)oxazoles with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex.
Xiao-Bao Shen,Yun Zhang,Wen-Xin Chen,Zheng-Kang Xiao,Ting-Ting Hu,Li-Xiong Shao,Li-Xiong Shao +6 more
TL;DR: Under the optimal conditions, various aryl chlorides were successfully applied as the aryalating reagents to achieve the 2-aryl (benzo)oxazoles in acceptable to high yields, providing a convenient and alternative method for the direct C-H bond arylation of (benzos) oxazoles and enriching the chemistry of the NHC-Pd(II) complex in organic synthesis.
Journal ArticleDOI
N-heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed direct C-H bond arylation of (benz)imidazoles with aryl chlorides.
TL;DR: The first example of sole direct C-H bond arylation of benzo[b]furans with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex, providing an efficient and economic pathway for the direct C2-H Bond arylated benzo-b-furans.
Journal ArticleDOI
Synthesis of 3,3‐Disubstituted Oxindoles by Palladium‐Catalyzed Asymmetric Intramolecular α‐Arylation of Amides: Reaction Development and Mechanistic Studies
Dmitry Katayev,Yi-Xia Jia,Yi-Xia Jia,Akhilesh K. Sharma,Dipshikha Banerjee,Céline Besnard,Raghavan B. Sunoj,E. Peter Kündig +7 more
TL;DR: Alkene additives to play an important role in increasing turnover number and frequency as catalysts for palladacycle intermediates resulting from the oxidative addition of [Pd(NHC)] into the aryl halide bond were isolated and structurally characterized.
Journal ArticleDOI
Facile Synthesis of 3-Aryloxindoles via Brønsted Acid Catalyzed Friedel–Crafts Alkylation of Electron-Rich Arenes with 3-Diazooxindoles
TL;DR: A simple metal-free method for the synthesis of 3-aryloxindole via Brønsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed and is proposed to proceed through acid-catalyzed protonation of3-diazonium ions followed by Friedel-Crafts-type alkylation of arenes.
Journal ArticleDOI
Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer.
TL;DR: An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed.
References
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Journal ArticleDOI
Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.
TL;DR: The 3,3'-pyrrolidinyl-spirooxindole unit is a privileged heterocyclic motif that forms the core of a large family of alkaloid natural products with strong bioactivity profiles and interesting structural properties.
Journal ArticleDOI
Palladium Complexes of N-Heterocyclic Carbenes as Catalysts for Cross-Coupling Reactions—A Synthetic Chemist's Perspective
TL;DR: The basics of Pd-NHC chemistry are discussed to understand the peculiarities of these catalysts and a critical discussion on their application in C-C and C-N cross-coupling as well as carbopalladation reactions is given.
Journal ArticleDOI
Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids
TL;DR: The spiro[pyrrolidine-3,3′-oxindole] ring system is found at the core of a number of alkaloids, which possess significant biological activity and are interesting, challenging targets for chemical synthesis as discussed by the authors.
Journal ArticleDOI
N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union
TL;DR: Cross-coupling reactions using Pd-NHC (NHC = N-heterocyclic carbene) catalysts are discussed in this critical review and examined in terms of catalytic activity and how these have permitted advances in the area as they developed.
Journal ArticleDOI
Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions.
Nicolas Marion,Steven P. Nolan +1 more
TL;DR: Four main classes of NHC-containing palladium(II) complexes will be presented: palladium dimers with bridging halogens, palladacycles, palladium acetates and acetylacetonates, and finally pi-allyl complexes.
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Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position
Feng Zhou,Yun-Lin Liu,Jian Zhou +2 more