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Literature DB >> 26403489

Iron-Catalyzed α-Alkylation of Ketones with Alcohols.

Saravanakumar Elangovan^1,2, Jean-Baptiste Sortais³, Matthias Beller², Christophe Darcel⁴.

Abstract

A general and benign iron-catalyzed α-alkylation reaction of ketones with primary alcohols has been developed. The key to success of the reaction is the use of a Knölker-type complex as catalyst (2 mol %) in the presence of Cs2 CO3 as base (10 mol %) under hydrogen-borrowing conditions. Using 2-aminobenzyl alcohol as alkylation reagent allows for the "green" synthesis of quinoline derivatives.

Entities: Chemical Gene

Keywords: Friedländer reaction; alkylation; borrowing hydrogen; homogeneous catalysis; iron catalysts

Year: 2015 PMID： 26403489 DOI： 10.1002/anie.201506698

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

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Cited

13 in total

Review 1. Borrowing Hydrogen for Organic Synthesis.

Authors: Benjamin G Reed-Berendt; Daniel E Latham; Mubarak B Dambatta; Louis C Morrill
Journal: ACS Cent Sci Date: 2021-03-25 Impact factor: 14.553

2. Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes.

Authors: Saravanakumar Elangovan; Jacob Neumann; Jean-Baptiste Sortais; Kathrin Junge; Christophe Darcel; Matthias Beller
Journal: Nat Commun Date: 2016-10-06 Impact factor: 14.919

3. Cyclometalated Ruthenium Pincer Complexes as Catalysts for the α-Alkylation of Ketones with Alcohols.

Authors: Patrick Piehl; Roberta Amuso; Elisabetta Alberico; Henrik Junge; Bartolo Gabriele; Helfried Neumann; Matthias Beller
Journal: Chemistry Date: 2020-03-09 Impact factor: 5.236

4. Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols.

Authors: Subrata Chakraborty; Prosenjit Daw; Yehoshoa Ben David; David Milstein
Journal: ACS Catal Date: 2018-10-02 Impact factor: 13.084

5. Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols.

Authors: Mubarak B Dambatta; Kurt Polidano; Alexander D Northey; Jonathan M J Williams; Louis C Morrill
Journal: ChemSusChem Date: 2019-05-07 Impact factor: 8.928

6. Hydrogen Transfer-Mediated Multicomponent Reaction for Direct Synthesis of Quinazolines by a Naphthyridine-Based Iridium Catalyst.

Authors: Zhenda Tan; Zhongxin Fu; Jian Yang; Yang Wu; Liang Cao; Huanfeng Jiang; Juan Li; Min Zhang
Journal: iScience Date: 2020-03-21

Iron-Catalyzed α-Alkylation of Ketones with Alcohols.

Review 1. Borrowing Hydrogen for Organic Synthesis.

2. Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes.

3. Cyclometalated Ruthenium Pincer Complexes as Catalysts for the α-Alkylation of Ketones with Alcohols.

4. Manganese-Catalyzed α-Alkylation of Ketones, Esters, and Amides Using Alcohols.

5. Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols.

6. Hydrogen Transfer-Mediated Multicomponent Reaction for Direct Synthesis of Quinazolines by a Naphthyridine-Based Iridium Catalyst.

7. One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation.

8. A Simple Iron-Catalyst for Alkenylation of Ketones Using Primary Alcohols.

9. Iron-Catalyzed Borrowing Hydrogen β-C(sp³)-Methylation of Alcohols.

10. Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN³ Pincer Catalyst.