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Direct Approach to N-Substituted-2-Fluoroindoles by Sequential Construction of C-N Bonds from gem-Difluorostyrenes

A mild and efficient synthesis of N-substituted-2-fluoroindole derivatives was achieved via Buchwald-Hartwig couplings and a sequential, base-promoted intramolecular nucleophilic reaction-beta-fluorine elimination. By employing easily obtained gem-difluorostyrenes and primary arylamines, the scope, advantages, and limitations of this reaction were well investigated. Furthermore, this strategy distinguishes itself by high modularity, operational simplicity, and a wide substrate scope, giving rise to a broad array of 2-fluoroindole derivatives in moderate to excellent yields.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Enantioselective and alpha-regioselective allylic amination of Morita-Baylis-Hillman acetates with simple aromatic amines catalyzed by planarly chiral ligand/palladium catalyst

An asymmetric allylic amination of Morita-Baylis-Hillman acetates with simple aromatic amines catalyzed by planarly chiral ligand/palladium-catalyst was developed in good yield with excellent alpha-regioselectivity (alpha/gamma up to 30:1) and moderate enantioselectivity (up to 70% ee).

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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A 3 – methyl – 1 – paratoluene sulfonyl tetrahydro pyrrole synthetic method of compound (by machine translation)

The invention discloses a 3 – methyl – 1 – paratoluene sulfonyl tetrahydro pyrrole compound synthesis method, is in the reaction solvent, in order to-activated alkyl halogenated hydrocarbon as reaction raw material, under the action of the metal palladium catalyst, reaction to obtain the multi-substituted 3 – methyl – 1 – paratoluene sulfonyl tetrahydro pyrrole compound. The invention mild reaction conditions, cheap raw material, the reaction operation is simple, the yield is high, for a large number of natural products and drug synthesis the provision of key frame structure, can be widely applied to the large-scale industrial production. (by machine translation)

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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An unusual dynamic Fe-Hg-Pd cluster with a palladium(0) fragment stabilized by d10-d10 heterometallic bonding

A heterometallic tetranuclear cluster resulting from an unprecedented metal-metal interaction is described in which a 14-electron PdL2 fragment is bonded to a Fe-Hg-Fe chain through helically arranged diphenylphosphanylmethane ligands (see picture), along which it exhibits an oscillating motion. The cluster exhibits a close contact between the Pd0 and Hg11 centers; the first such d10-d10 interaction to have been observed.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Michael Acceptors: Construction of Vicinal Quaternary Stereocenters

An efficient method for the diastereo- and enantioselective construction of vicinal all-carbon quaternary stereocenters through palladium-catalyzed decarboxylative cycloaddition of vinylethylene carbonates with activated Michael acceptors was developed. By using a palladium complex generated insitu from [Pd2(dab)3]CHCl3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process provides multifunctionalized tetrahydrofurans bearing vicinal all-carbon quaternary stereocenters in high yields with a high level of absolute and relative stereocontrol.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Bromobis(triphenylphosphine)(N-succinimide)palladium(II) as a novel catalyst for Stille cross-coupling reactions

A new palladium catalyst is reported for Stille cross-coupling, namely [Pd(NCOC2H4CO)(PPh3)2Br].

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-catalysed Preparation of 1,2-Dienes by Selective Hydrogenolysis of Alk-2-ynyl Cabonates with Ammonium Formate

1,2-Dienes were prepared by the selective hydrogenolysis of alk-2-ynyl carbonates with HCO2NH4 catalysed by Pd2(dba)3*CHCl3-P(n-Bu)3 (dba = dibenzylideneacetone).

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium Catalysed Direct Allylation of Pronucleophiles with Allylstannanes

The reaction of pronucleophiles 1 with allyltributylstannanes in the presence of catalytic amounts of Pd2(dba)3*CHCl3 (4 molpercent) and 1,2-bis(diphenylphosphino)ethane (dppe) (10 molpercent) at room temperature gives the corresponding allylation products in good to high yields.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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A novel methodology for the synthesis of cyclic carbonates based on the palladium-catalyzed cascade reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, involving a novel carbon dioxide elimination-fixation process

A palladium-catalyzed CO2-recycling reaction has been developed. Reaction of 4-methoxycarbonyloxy-2-butyn-1-ols with phenols, carried out in the presence of a palladium catalyst, produces phenoxy-substituted cyclic carbonates by way of a pathway involving a CO2 elimination-fixation. A variety of propargylic alcohols and phenols participate in these reactions which yield cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. Highly enantioselective reactions occur when (S)-BINAP is used as a ligand. Reaction of 4-phenoxycarbonyloxy-2-butyn-1-ol in the presence of the palladium catalyst yields the corresponding cyclic carbonates via a three-component decomposition-reconstruction process.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Palladium-Catalyzed Three-Component Reaction of 3-(Tri-n- butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using alpha,gamma-Substituted Allylic Tin Reagents

A three-component reaction of 3-(tri-n-butylstannyl)allyl acetates, aldehydes, and triorganoboranes in the presence of a palladium-Xantphos catalyst system predominately gave (E)-anti-homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem-palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of the in-situ-generated (E)-vinylpalladium acetate with the triorganoborane.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method