Palladium-catalyzed Annulation Reaction Research Articles

Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis

Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and, where applicable, diastereoselectivities. This method provides rapid assembly of building blocks for natural product synthesis, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.

ChemInform Abstract: Prop-2-ynylic Carbonates as a1,a2 Synthons in Palladium Catalyzed Annulation Reactions with Bifunctional Nucleophiles.

ChemInform Abstract: Prop-2-ynylic Carbonates as a1,a2 Synthons in Palladium Catalyzed Annulation Reactions with Bifunctional Nucleophiles.

ChemInform Abstract: Acenaphth(1,2-a)acenaphthylene: A Semi-Benzenoid Hydrocarbon with Dienophilic Central Double Bond.

Abstract A palladium catalyzed annulation reaction leads to the title compound 3 in a single preparative step. The reactivity of the strained central double bond is highlighted by the cyloaddition reaction with anthracene.

ChemInform Abstract: Palladium-Catalyzed Annulation Reaction of o-Bromobenzaldehydes with Carbonyl Compounds to Produce Naphthol and/or Naphthalene Derivatives.

ChemInform Abstract: Palladium-Catalyzed Annulation Reaction of o-Bromobenzaldehydes with Carbonyl Compounds to Produce Naphthol and/or Naphthalene Derivatives.

Palladium-Catalyzed Annulation of 2-(1-Alkynyl)biphenyls with Aryl Iodides to Disubstituted Methylidenefluorenes.

The palladium-catalyzed annulation reaction of 2-(1-alkynyl)biphenyls (1) with aryl iodides has been developed to prepare a variety of diarylmethylidenefluorenes (2). This method tolerates various functional groups in aryl iodide, such as OCH(3), CH(3), Cl, Br, Cf(3), and NO(2). All proceed in good yield with the exception of 4-iodonitrobenzene.

Norbornadiene as an Acetylene Synthon in Palladium-Catalyzed Annulation Reactions

Norbornadiene as an Acetylene Synthon in Palladium-Catalyzed Annulation Reactions

Regioselective One-Step Synthesis of 4-Fluoroalkylated Isoquinolines via Carbopalladation Reaction of Fluorine-Containing Alkynes

[reaction: see text] The palladium-catalyzed annulation reaction of fluoroalkylated alkynes with various 2-iodobenzylidenamines was investigated. In the presence of a catalytic amount of Pd(PPh3)4, the reaction took place smoothly to give the corresponding 4-fluoroalkylated isoquinoline in high yield as a single isomer. No other regioisomer was detected.

A First Regioselective Synthesis of 3‐Fluoroalkylated Benzofurans via Palladium‐Catalyzed Annulation of Fluorine‐Containing Internal Alkynes with Variously Substituted 2‐Iodophenol.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Highly Regioselective Palladium-Catalyzed Annulation Reactions of Heteroatom-Substituted Allenes for Synthesis of Condensed Heterocycles

We have developed a highly regioselective synthesis of heterocycles via palladium-catalyzed annulation reaction of heteroatom-substituted allenes. Various aryl halides were reacted and one regioisomer was observed exclusively in all reactions. In addition, subsequent functionalizations of annulated products were carried out using alkyl metal reagents, and the introduction of alkyl moieties was accomplished.

A first regioselective synthesis of 3-fluoroalkylated benzofurans via palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodophenol

The palladium-catalyzed annulation reaction of a variety of fluorine-containing internal alkynes with 2-iodophenol derivatives was investigated. The use of P( t-Bu) 3 as a ligand on palladium was found to be crucial in this annulation reaction, resulting in the exclusive formation of 3-fluoroalkylated benzofurans in high yields. 19F NMR analysis of the reaction mixture revealed that the addition of phenol to the fluoroalkylated alkynes was followed by intramolecular Heck reaction, giving to the corresponding 3-fluoroalkylated benzofurans.

A Facile Synthesis of Various Fluorine‐Containing Indole Derivatives via Palladium‐Catalyzed Annulation of Internal Alkynes.

AbstractFor Abstract see ChemInform Abstract in Full Text.

A Facile Synthesis of Various Fluorine-Containing Indole Derivatives via Palladium-Catalyzed Annulation of Internal Alkynes

The palladium-catalyzed annulation reaction of a variety of fluorine-containing internal alkynes with 2-iodoaniline derivatives took place smoothly to give the corresponding 2,3-disubstituted indole derivatives in good to excellent yields.

Dibenzo[g,p]chrysene, a Novel Core for Discotic Liquid Crystals

Dibenzo[g,p]chrysene, a new π-conjugated polycyclic aromatic hydrocarbon, has been found to function as the core fragment for the preparation of discotic liquid crystals. First two derivatives of this novel core were prepared by a palladium-catalyzed annulation reaction of diphenylacetylenes with 2-iodobiaryls, followed by oxidative coupling. Charge-transfer interactions that induced columnar mesophase formation was observed in both the compounds. Their mesomorphic behavior was studied by polarizing microscopy and differential scanning calorimetry.

Synthetic Application of Sequential Palladium-Catalyzed Allylic Acetate Alkylation and Michael Addition Carbocyclization: Synthesis of (±)-Dihydroerythramine

A new synthetic route to aromatic Erythrina alkaloids is reported. (Nitromethyl)arene 3 underwent a palladium-catalyzed annulation reaction with allylic acetate 11 to provide nitro esters 12a and 12b by an (η3-allyl)palladium complex alkylation/Michael addition domino sequence. Reduction of the nitro group of 12a, followed by cyclization of the resulting amino group on the acetate appendage, afforded the bicyclic lactam 29. Two-carbon elongation at the nitrogen atom of 29 by hetero Michael addition of vinyl phenyl sulfoxide, followed by Pummerer-type cyclization, gave cis-11-phenylthioerythrinan-8-one (32a, 32b) along with the rearranged lactam 34. Reductive desulfurization at C-11, and oxidative cleavage of the C-3 exocyclic double bond afforded the 15,16-(methylenedioxy)erythrinan-3,8-dione (42). Reduction of the C-3 carbonyl group and methylation of the resulting alcohol afforded hexahydrocrystamidine (44), which was further reduced by aluminum hydride to give (±)-dihydroerythramine (9).

Palladium-Catalyzed Annulation Reaction of o-Bromobenzaldehydes with Carbonyl Compounds to Produce Naphthol and/or Naphthalene Derivatives

o-Bromobenzaldehydes undergo annulation with 1,3-diaryl-2-propanones in the presence of a palladium catalyst to give the corresponding 1,3-diaryl-2-naphthols in fair to good yields. From the reaction of the aldehydes with 2-substituted 2-alkenals are formed 2,4-disubstituted 1-naphthols and/or 1,3-disubstituted naphthalenes accompanied by decarbonylation.

A palladium catalyzed domino coupling process to substituted phenanthrenes

A palladium catalyzed annulation reaction of diphenylacetylene with iodobenzene leads to 9,10-diphenylphenanthrene. The regiochemistry of this domino coupling process is studied, suggesting the cis-trans isomerization of vinyl palladium complexes as reactive intermediates.

Transition metal catalyzed annulation reactions. Part 3. Palladium-catalyzed annulation reactions of 1,8-diiodonaphthalene

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTransition metal catalyzed annulation reactions. Part 3. Palladium-catalyzed annulation reactions of 1,8-diiodonaphthaleneGerald DykerCite this: J. Org. Chem. 1993, 58, 1, 234–238Publication Date (Print):January 1, 1993Publication History Published online1 May 2002Published inissue 1 January 1993https://doi.org/10.1021/jo00053a042RIGHTS & PERMISSIONSArticle Views1496Altmetric-Citations81LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (483 KB) Get e-Alerts Get e-Alerts

Acenaphth[1,2-a]acenaphthylene: a semi-benzenoid hydrocarbon with dienophilic central double bond

A palladium catalyzed annulation reaction leads to the title compound in a single preparative step.

Palladium catalyzed annulation reaction using a bifunctional allylic alkylating agent

Methylene-cyclopentane and -cyclohexane derivatives were synthesized by the reaction of 2-methylene-propane-1,3-diol diacetate with dicarbanions under the palladium catalysis.