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Literature DB >> 23001913

Multicomponent assembly of highly substituted indoles by dual palladium-catalyzed coupling reactions.

John M Knapp¹, Jie S Zhu, Dean J Tantillo, Mark J Kurth.

Abstract

Highly substituted indoles were synthesized by a palladium-catalyzed reaction involving three independent components in a one-pot reaction. Two distinct palladium-catalyzed coupling reactions occur with a single catalytic system: a Buchwald-Hartwig reaction and an arene-alkene coupling. Quantum chemical computations provide insight into the mechanism of the latter coupling step.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2012 PMID： 23001913 PMCID： PMC3517165 DOI： 10.1002/anie.201204633

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

39 in total

Review 1. Isolation and synthesis of biologically active carbazole alkaloids.

Authors: Hans-Joachim Knölker; Kethiri R Reddy
Journal: Chem Rev Date: 2002-11 Impact factor: 60.622

2. Palladium-catalyzed tandem alkenyl and aryl C--N bond formation: a cascade N-annulation route to 1-functionalized indoles.

Authors: Michael C Willis; Gareth N Brace; Ian P Holmes
Journal: Angew Chem Int Ed Engl Date: 2005-01-07 Impact factor: 15.336

3. Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors: Sandro Cacchi; Giancarlo Fabrizi
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

4. The azaallylic anion as a synthon for pd-catalyzed synthesis of heterocycles: domino two- and three-component synthesis of indoles.

Authors: José Barluenga; Agustín Jiménez-Aquino; Carlos Valdés; Fernando Aznar
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Palladium-catalyzed aryl amination-heck cyclization cascade: a one-flask approach to 3-substituted indoles.

Authors: Thomas Jensen; Henrik Pedersen; Benny Bang-Andersen; Robert Madsen; Morten Jørgensen
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

Review 6. Multi-component syntheses of heterocycles by transition-metal catalysis.

Authors: Daniel M D'Souza; Thomas J J Müller
Journal: Chem Soc Rev Date: 2007-02-19 Impact factor: 54.564

7. Synthesizing our future.

Authors: Ryoji Noyori
Journal: Nat Chem Date: 2009-04 Impact factor: 24.427

8. The role of reversible oxidative addition in selective palladium(0)-catalyzed intramolecular cross-couplings of polyhalogenated substrates: synthesis of brominated indoles.

Authors: Stephen G Newman; Mark Lautens
Journal: J Am Chem Soc Date: 2010-08-25 Impact factor: 15.419

9. Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization.

Authors: Yusuke Ohta; Hiroaki Chiba; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal: J Org Chem Date: 2009-09-18 Impact factor: 4.354

6. A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions.

Authors: Xiaodong Tang; Songlei Zhu; Ying Ma; Ren Wen; Lanqi Cen; Panwei Gong; Jing Wang
Journal: Molecules Date: 2018-11-20 Impact factor: 4.411

6 in total

Multicomponent assembly of highly substituted indoles by dual palladium-catalyzed coupling reactions.

Review 1. Isolation and synthesis of biologically active carbazole alkaloids.

2. Palladium-catalyzed tandem alkenyl and aryl C--N bond formation: a cascade N-annulation route to 1-functionalized indoles.

3. Synthesis and functionalization of indoles through palladium-catalyzed reactions.

4. The azaallylic anion as a synthon for pd-catalyzed synthesis of heterocycles: domino two- and three-component synthesis of indoles.

5. Palladium-catalyzed aryl amination-heck cyclization cascade: a one-flask approach to 3-substituted indoles.

Review 6. Multi-component syntheses of heterocycles by transition-metal catalysis.

7. Synthesizing our future.

8. The role of reversible oxidative addition in selective palladium(0)-catalyzed intramolecular cross-couplings of polyhalogenated substrates: synthesis of brominated indoles.

9. Construction of nitrogen heterocycles bearing an aminomethyl group by copper-catalyzed domino three-component coupling-cyclization.

10. Amines as key building blocks in Pd-assisted multicomponent processes.

1. Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

2. Total Synthesis of (-)-Nodulisporic Acid D.

3. Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-alkylation/tandem cyclization.

4. Microwave-assisted synthesis of 3-nitroindoles from N-aryl enamines via intramolecular arene-alkene coupling.

5. Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

6. A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions.