Palladium-catalysed synthesis of heterocondensed pyrroles

Wensbo, David; Eriksson, A.; Jeschke, Torsten; Annby, Ulf; Gronowitz, Salo; Cohen, Louis A.

doi:10.1016/s0040-4039(00)73572-6

Cited by 87 publications

(23 citation statements)

References 26 publications

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“…While changing the aryl moiety at the diyne, the yields of 2 h-2 j decreased slightly independent of the substitution pattern whereas the fluorescent acetophenone derivative 2 l was obtained in 86 % demonstrating the facile access to a variety of compounds. To our surprise, when the pyridine derivatives, generally not troublesome in carbopalladation chemistry, [8] were exposed to our reaction conditions no conversion to 2 g or only traces of 2 k were observed (cf. mechanistic investigations).…”

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confidence: 80%

Formal anti‐Carbopalladation Reactions of Non‐Activated Alkynes: Requirements, Mechanistic Insights, and Applications

et al. 2015

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Formal anti-carbopalladation reactions of CC triple bonds are uncommon, but highly useful transformations. Alkynes can be designed to give anti-carbopalladation products. Prerequisite is the exclusion of other reaction pathways to provoke the cis-trans isomerization of the syn-carbopalladation intermediate. Detailed mechanistic studies of this crucial step by experimental and computational means were performed. Application of an intramolecular version for the synthesis of oligocyclic compounds and substituted dibenzofurans is also described.

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confidence: 80%

Formal anti‐Carbopalladation Reactions of Non‐Activated Alkynes: Requirements, Mechanistic Insights, and Applications

et al. 2015

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“…18 They found that reaction with trimethylsilylacetylene generally gave complex reaction mixtures. 18 They found that reaction with trimethylsilylacetylene generally gave complex reaction mixtures.…”

Section: Construction Of Azaindoles Via Transition-metal Mediated Promentioning

confidence: 99%

Organometallic methods for the synthesis and functionalization of azaindoles

et al. 2007

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Azaindoles (also called pyrrolopyridines) constitute essential subunits in many pharmaceutically important compounds. The synthesis of azaindoles has been a great synthetic challenge for chemists. Many classical methods for indole synthesis (such as Fischer and Madelung cyclizations) often cannot be effectively applied to the synthesis of the corresponding azaindoles. In recent years, advances in organometallic chemistry have enabled a number of novel and efficient methodologies for azaindole formation as well as for the further functionalization of azaindole templates. In this tutorial review, we have surveyed the recent development of organometallic chemistry-based methods for azaindole synthesis.

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“…This includes work on solid supports [62], the use of heteroaryl spacers [63], the construction of polycyclic products [64], and, more recently, moving from aryl iodides to less expensive aryl bromides and aryl chlorides [65]. The latter was demonstrated by Senanayke and coworkers with the use of the now common bulky electron-rich phosphines to activate the aryl-chloride bond for cyclization (Scheme 6.48).…”

Section: Palladium-catalyzed Carbon-oxygen Bond Formationmentioning

confidence: 99%

The Palladium‐Catalyzed Synthesis of Aromatic Heterocycles

Arndtsen

2010

Catalyzed Carbon‐Heteroatom Bond Formation

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Palladium-catalysed synthesis of heterocondensed pyrroles

Cited by 87 publications

References 26 publications

Formal anti‐Carbopalladation Reactions of Non‐Activated Alkynes: Requirements, Mechanistic Insights, and Applications

Formal anti‐Carbopalladation Reactions of Non‐Activated Alkynes: Requirements, Mechanistic Insights, and Applications

Organometallic methods for the synthesis and functionalization of azaindoles

The Palladium‐Catalyzed Synthesis of Aromatic Heterocycles

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