Journal ArticleDOI
Palladium-Catalyzed Acylation/Alkenylation of Aryl Iodide: A Domino Approach Based on the Catellani–Lautens Reaction
Ping-Xin Zhou,Yu-Ying Ye,Ce Liu,Lian-Biao Zhao,Jian-Ye Hou,Dao-Qian Chen,Qian Tang,An-Qi Wang,Jie-Yu Zhang,Qi-Xing Huang,Peng-Fei Xu,Yong-Min Liang +11 more
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TLDR
This reaction is the first example of introducing an acyl group at the ortho position of aryl iodides, and the proposed PdIV complex, generated via oxidative addition of the carboxylic anhydrides, is a key intermediate for this transformation.Abstract:
A new palladium-catalyzed three-component coupling involving acylation/alkenylation of aryl iodide is reported. The reaction was carried out with readily available starting materials and gave the ortho-acylated styrene in moderate to good yields. Compared with previous Catellani–Lautens reactions, this reaction is the first example of introducing an acyl group at the ortho position of aryl iodides. The proposed PdIV complex, generated via oxidative addition of the carboxylic anhydrides, is a key intermediate for this transformation.read more
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Journal ArticleDOI
Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis
TL;DR: The emergence of transient directing group approaches through the in situ installation and deconstruction of a Lewis-basic entity with the aid of co-catalytic additives for selective C–H functionalizations is discussed.
Journal ArticleDOI
Metal–Organic Cooperative Catalysis in C–H and C–C Bond Activation
TL;DR: This review discusses various metal-organic cooperative catalytic systems developed for C-H and C-C bond activation reactions, which proceed with high efficiencies and selectivities.
Journal ArticleDOI
Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C-H Bond Activation.
TL;DR: A synthetic methodology is discovered that combines selective C-H bond activation with sequential reactions that enables the selective functionalization of both the ortho and ipso positions of aryl halides and relates to alkylation and arylation reactions.
Journal ArticleDOI
Palladium-catalysed norbornene-mediated C-H functionalization of arenes.
Juntao Ye,Mark Lautens +1 more
TL;DR: The Catellani reaction--a palladium-catalysed C-H functionalization reaction mediated by norbornene--was first reported in 1997 and dramatic progress has been made in the past five years, including applications in natural products synthesis.
Journal ArticleDOI
Palladium/Norbornene Cooperative Catalysis.
Jianchun Wang,Guangbin Dong +1 more
TL;DR: This Review provides a comprehensive overview of Palladium/norbornene cooperative catalysis, including the early stoichiometric investigations, catalytic reaction developments, as well as the applications in the syntheses of bioactive compounds and polymers.
References
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Journal ArticleDOI
Emergence of palladium(IV) chemistry in synthesis and catalysis.
TL;DR: The need to comprehensively review catalytic PdIV chemistry, particularly in organic synthesis, was identified, which draws on aspects from both inorganic (organometallic) and organic chemistry fields, and the historical background to organopalladium(IV) chemistry is detailed.
Journal ArticleDOI
Catalytic sequential reactions involving palladacycle-directed aryl coupling steps.
TL;DR: This Account reports the methodology, based on the cooperative action of Pd and norbornene, that achieves selective aryl-aryl coupling through C-halide and C-H activation, and obtained the key metallacycle able to selectively direct the reactions by replacing nor Bornene with an aryL-bonded aminocarbonyl group.
Journal ArticleDOI
Use of solid catalysts in Friedel-Crafts acylation reactions.
Giovanni Sartori,Raimondo Maggi +1 more
Journal ArticleDOI
Pd(II)-Catalyzed Regioselective 2-Alkylation of Indoles via a Norbornene-Mediated C–H Activation: Mechanism and Applications
TL;DR: A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles was developed based on a norbornene-mediated regioselective cascade C-H activation, and two structurally different Aspidosperma alkaloids were synthesized in concise routes.
Journal ArticleDOI
A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction.
TL;DR: A norbornene-mediated palladium-catalyzed tandem alkylation/C-H functionalization sequence is described, in which an alkyl-aryl bond and a heteroaryl- Daryl bond are formed in one pot.
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Ortho vs ipso: site-selective Pd and norbornene-catalyzed arene C-H amination using aryl halides.
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Palladium-catalysed norbornene-mediated C-H functionalization of arenes.
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