Literature DB >> 18260672

A palladium-catalyzed alkylation/direct arylation synthesis of nitrogen-containing heterocycles.

Christophe Blaszykowski1, Evangelos Aktoudianakis, Dino Alberico, Cyril Bressy, David G Hulcoop, Farnaz Jafarpour, Arash Joushaghani, Benoît Laleu, Mark Lautens.   

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.

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Year:  2008        PMID: 18260672     DOI: 10.1021/jo702052b

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Heterocyclic chemistry: New reactivity realized.

Authors:  Timothy C Gallagher
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

2.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

3.  C-H bonds as ubiquitous functionality: a general approach to complex arylated pyrazoles via sequential regioselective C-arylation and N-alkylation enabled by SEM-group transposition.

Authors:  Roman Goikhman; Teresa L Jacques; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

4.  Pd-catalyzed dehydrogenative annulation approach for the efficient synthesis of phenanthridinones.

Authors:  Xinyao Li; Jun Pan; Song Song; Ning Jiao
Journal:  Chem Sci       Date:  2016-04-26       Impact factor: 9.825

5.  Homogeneous and Gas-Liquid Catellani-Type Reaction Enabled by Continuous-Flow Chemistry.

Authors:  Alessandra Casnati; Hannes P L Gemoets; Elena Motti; Nicola Della Ca'; Timothy Noël
Journal:  Chemistry       Date:  2018-08-28       Impact factor: 5.236

  5 in total

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