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Literature DB >> 30505062

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols.

Abstract

The cationic ruthenium-hydride complex catalyzes dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.

Entities: Chemical Disease Gene

Year: 2016 PMID： 30505062 PMCID： PMC6261509 DOI： 10.1021/acs.organomet.6b00273

Source DB: PubMed Journal: Organometallics ISSN： 0276-7333 Impact factor: 3.876

32 in total

Review 1. Cyclometalation using d-block transition metals: fundamental aspects and recent trends.

Authors: Martin Albrecht
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

2. Chemoselective Pd-catalyzed oxidation of polyols: synthetic scope and mechanistic studies.

Authors: Kevin Chung; Steven M Banik; Antonio G De Crisci; David M Pearson; Timothy R Blake; Johan V Olsson; Andrew J Ingram; Richard N Zare; Robert M Waymouth
Journal: J Am Chem Soc Date: 2013-05-09 Impact factor: 15.419

3. Ruthenium(II) terdentate CNN complexes: superlative catalysts for the hydrogen-transfer reduction of ketones by reversible insertion of a carbonyl group into the Ru-H bond.

Authors: Walter Baratta; Giorgio Chelucci; Serafino Gladiali; Katia Siega; Micaela Toniutti; Matteo Zanette; Ennio Zangrando; Pierluigi Rigo
Journal: Angew Chem Int Ed Engl Date: 2005-09-26 Impact factor: 15.336

4. Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: indole synthesis from anilines and ketones.

Authors: Ye Wei; Indubhusan Deb; Naohiko Yoshikai
Journal: J Am Chem Soc Date: 2012-05-24 Impact factor: 15.419

5. Hydrogen transfer to carbonyls and imines from a hydroxycyclopentadienyl ruthenium hydride: evidence for concerted hydride and proton transfer.

Authors: C P Casey; S W Singer; D R Powell; R K Hayashi; M Kavana
Journal: J Am Chem Soc Date: 2001-02-14 Impact factor: 15.419

1. Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.

Authors: Hanbin Lee; Manoj V Mane; Ho Ryu; Debashis Sahu; Mu-Hyun Baik; Chae S Yi
Journal: J Am Chem Soc Date: 2018-08-03 Impact factor: 15.419

1 in total

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols.

Review 1. Cyclometalation using d-block transition metals: fundamental aspects and recent trends.

2. Chemoselective Pd-catalyzed oxidation of polyols: synthetic scope and mechanistic studies.

3. Ruthenium(II) terdentate CNN complexes: superlative catalysts for the hydrogen-transfer reduction of ketones by reversible insertion of a carbonyl group into the Ru-H bond.

4. Palladium-catalyzed aerobic oxidative cyclization of N-aryl imines: indole synthesis from anilines and ketones.

5. Hydrogen transfer to carbonyls and imines from a hydroxycyclopentadienyl ruthenium hydride: evidence for concerted hydride and proton transfer.

6. Chiral Cyclopentadienyls: Enabling Ligands for Asymmetric Rh(III)-Catalyzed C-H Functionalizations.

7. Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols.

8. Indoles from simple anilines and alkynes: palladium-catalyzed C-H activation using dioxygen as the oxidant.

9. Redox-Neutral Couplings between Amides and Alkynes via Cobalt(III)-Catalyzed C-H Activation.

10. Cobalt(III)-Catalyzed Redox-Neutral Synthesis of Unprotected Indoles Featuring an N-N Bond Cleavage.

1. Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.