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Literature DB >> 20141119

Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reactions.

Abstract

A new method for the synthesis of tricyclic nitrogen heterocycles from N,2-diallylaniline derivatives is described. These transformations proceed via sequential alkene aminopalladation of an intermediate L(n)Pd(Ar)(NRR') species followed by alkene carbopalladation of the resulting L(n)Pd(Ar)(R) complex. Both alkene insertion steps occur in preference to C-N or C-C bond-forming reductive elimination. An unusual 1,3-palladium shift occurs when 2-Allyl-N-(2-vinylphenyl)aniline is employed as substrate, which yields a tetracyclic molecule with three contiguous stereocenters.

Entities: Chemical

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Year: 2010 PMID： 20141119 PMCID： PMC2830278 DOI： 10.1021/ol100033s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

13 in total

1. Reductive elimination of aryl halides from palladium(II).

Authors: A H Roy; J F Hartwig
Journal: J Am Chem Soc Date: 2001-02-14 Impact factor: 15.419

Review 2. Synthesis of heterocycles via palladium-catalyzed oxidative addition.

Authors: Gilson Zeni; Richard C Larock
Journal: Chem Rev Date: 2006-11 Impact factor: 60.622

3. Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.

Authors: John P Wolfe
Journal: European J Org Chem Date: 2007-02

4. Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

Authors: Ricardo Lira; John P Wolfe
Journal: J Am Chem Soc Date: 2004-11-03 Impact factor: 15.419

5. Synthesis of benzo-fused 1-azabicyclo[m.n.0]alkanes via the Schmidt reaction: a formal synthesis of gephyrotoxin.

Authors: W H Pearson; W Fang
Journal: J Org Chem Date: 2000-10-20 Impact factor: 4.354

6. Antimicrobial activities of a new schizozygane indoline alkaloid from Schizozygia coffaeoides and the revised structure of isoschizogaline.

Authors: R M Kariba; P J Houghton; Abiy Yenesew
Journal: J Nat Prod Date: 2002-04 Impact factor: 4.050

7. Pd-catalyzed alkyl to aryl migration and cyclization: an efficient synthesis of fused polycycles via multiple C-H activation.

Authors: Qinhua Huang; Alessia Fazio; Guangxiu Dai; Marino A Campo; Richard C Larock
Journal: J Am Chem Soc Date: 2004-06-23 Impact factor: 15.419

4. Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines.

Authors: Dongari Yadagiri; Angula Chandra Shekar Reddy; Pazhamalai Anbarasan
Journal: Chem Sci Date: 2016-05-24 Impact factor: 9.825

4 in total

Synthesis of polycyclic nitrogen heterocycles via alkene aminopalladation/carbopalladation cascade reactions.

1. Reductive elimination of aryl halides from palladium(II).

Review 2. Synthesis of heterocycles via palladium-catalyzed oxidative addition.

3. Palladium-Catalyzed Carboetherification and Carboamination Reactions of γ-Hydroxy- and γ-Aminoalkenes for the Synthesis of Tetrahydrofurans and Pyrrolidines.

4. Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

5. Synthesis of benzo-fused 1-azabicyclo[m.n.0]alkanes via the Schmidt reaction: a formal synthesis of gephyrotoxin.

6. Antimicrobial activities of a new schizozygane indoline alkaloid from Schizozygia coffaeoides and the revised structure of isoschizogaline.

7. Pd-catalyzed alkyl to aryl migration and cyclization: an efficient synthesis of fused polycycles via multiple C-H activation.

8. Rapid construction of five contiguous stereocenters in a multi-cascade reaction.

9. Isatisine A, a novel alkaloid with an unprecedented skeleton from leaves of Isatis indigotica.

10. Efficient construction of tri- and tetracyclic heterocycles from linear 1,6-dienes by a domino reaction.

1. Gold-catalyzed three-component coupling: oxidative oxyarylation of alkenes.

2. Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

3. A one-pot multicomponent strategy for stereospecific construction of tricyclic pyrrolo[1,2-a]quinolines.

4. Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from N-sulfonyl-1,2,3-triazoles and ortho-vinylanilines.