Journal ArticleDOI
A palladium-catalyzed alkylation/direct arylation synthesis of nitrogen-containing heterocycles.
Christophe Blaszykowski,Evangelos Aktoudianakis,Dino Alberico,Cyril Bressy,David G. Hulcoop,Farnaz Jafarpour,Arash Joushaghani,Benoît Laleu,Mark Lautens +8 more
TLDR
A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel.Abstract:
A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.read more
Citations
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Recent advances in aryl–aryl bond formation by direct arylation
TL;DR: Compared to traditional methods, direct arylation affords Ar-Ar compounds in fewer steps by removing the need for prefunctionalisation, and given that either one or two hydrogens are targeted, less waste and good atom economy are features of this methodology.
Journal ArticleDOI
Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.
Fabio Bellina,Renzo Rossi +1 more
TL;DR: New, effective, and more environmentallybenignmethodologiesfortheformation of(cyclo)alkyl-aryl bonds, which require a reduced number of synthetic operations, have emerged as valuable alternatives to the conventional cross-coupling reactions.
Journal ArticleDOI
Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds
TL;DR: Conditions for the palladium-catalyzed direct arylation of a wide range of heterocycles with aryl bromides are reported and employ a stoichiometric ratio of both coupling partners, as well as a substoichiometric quantity of pivalic acid, which results in significantly faster reactions.
Journal ArticleDOI
Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C–H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates
Fabio Bellina,Renzo Rossi +1 more
Journal ArticleDOI
Transition Metal-Catalyzed CH Activation of Indoles
TL;DR: Recent advances and strategies for transition metal-catalyzed CH activation of indoles and a versatile tool box for the preparation of structurally diverse indoles are discussed.
References
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Journal ArticleDOI
Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.
Journal ArticleDOI
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.
TL;DR: A number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, but the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps.
BookDOI
Handbook of organopalladium chemistry for organic synthesis
TL;DR: Palladium-CATALYZED Reactions Involving Nucleophilic Attack on -Ligands of Palladium-Alkene, PalladiumAlkyne, and Related Derivatives as mentioned in this paper.
Journal ArticleDOI
Practical methodologies for the synthesis of indoles.
Journal ArticleDOI