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Literature DB >> 18761437

Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

W C Peter Tsang¹, Rachel H Munday, Gordon Brasche, Nan Zheng, Stephen L Buchwald.

Abstract

The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.

Entities: Chemical Disease Species

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Year: 2008 PMID： 18761437 PMCID： PMC2748774 DOI： 10.1021/jo801273q

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

66 in total

1. Activation of Cminus signH Bonds by Metal Complexes.

Authors: Alexander E. Shilov; Georgiy B. Shul'pin
Journal: Chem Rev Date: 1997-12-18 Impact factor: 60.622

2. Palladium-catalyzed arylative carbon-carbon bond cleavage of alpha,alpha-disubstituted arylmethanols.

Authors: Y Terao; H Wakui; T Satoh; M Miura; M Nomura
Journal: J Am Chem Soc Date: 2001-10-24 Impact factor: 15.419

3. Mechanistic study of alcohol oxidation by the Pd(OAc)(2)/O(2)/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts.

Authors: Bradley A Steinhoff; Shannon R Fix; Shannon S Stahl
Journal: J Am Chem Soc Date: 2002-02-06 Impact factor: 15.419

4. Ellipticine derivatives.

Authors: R W Guthrie; A Brossi; F A Mennona; J G Mullin; R W Kierstead; E Grunberg
Journal: J Med Chem Date: 1975-07 Impact factor: 7.446

5. Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes.

Authors: S Lamansky; P Djurovich; D Murphy; F Abdel-Razzaq; H E Lee; C Adachi; P E Burrows; S R Forrest; M E Thompson
Journal: J Am Chem Soc Date: 2001-05-09 Impact factor: 15.419

6. Light-emitting carbazole derivatives: potential electroluminescent materials.

Authors: K R Thomas; J T Lin; Y T Tao; C W Ko
Journal: J Am Chem Soc Date: 2001-09-26 Impact factor: 15.419

7. Catalytic functionalization of arenes and alkanes via C-H bond activation.

Authors: C Jia; T Kitamura; Y Fujiwara
Journal: Acc Chem Res Date: 2001-08 Impact factor: 22.384

Review 8. Stereoselective total synthesis of axially chiral natural products via biaryl lactones.

Authors: G Bringmann; D Menche
Journal: Acc Chem Res Date: 2001-08 Impact factor: 22.384

9. Synthesis and characterization of monodendrons based on 9-phenylcarbazole

Authors:
Journal: J Org Chem Date: 2000-01-14 Impact factor: 4.354

10. Siamenol, a new carbazole alkaloid from Murraya siamensis.

Authors: K M Meragelman; T C McKee; M R Boyd
Journal: J Nat Prod Date: 2000-03 Impact factor: 4.050

20 in total

1. Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

Authors: Alison N Campbell; Shannon S Stahl
Journal: Acc Chem Res Date: 2012-01-23 Impact factor: 22.384

Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

1. Activation of Cminus signH Bonds by Metal Complexes.

2. Palladium-catalyzed arylative carbon-carbon bond cleavage of alpha,alpha-disubstituted arylmethanols.

3. Mechanistic study of alcohol oxidation by the Pd(OAc)(2)/O(2)/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts.

4. Ellipticine derivatives.

5. Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes.

6. Light-emitting carbazole derivatives: potential electroluminescent materials.

7. Catalytic functionalization of arenes and alkanes via C-H bond activation.

Review 8. Stereoselective total synthesis of axially chiral natural products via biaryl lactones.

9. Synthesis and characterization of monodendrons based on 9-phenylcarbazole

10. Siamenol, a new carbazole alkaloid from Murraya siamensis.

1. Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

2. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

3. Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

4. Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization.

5. Regioselective C-H bond amination by aminoiodanes.

6. Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

7. Examination of the mechanism of Rh(2)(II)-catalyzed carbazole formation using intramolecular competition experiments.

8. Palladium Catalyzed Aryl C-H Amination with O₂ via In Situ Formation of Peroxide-Based Oxidant(s) from Dioxane.

9. Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

10. Intramolecular Ir(I)-catalyzed benzylic C-H bond amination of ortho-substituted aryl azides.