Literature DB >> 27785889

Manganese-Catalyzed Hydrogen-Autotransfer C-C Bond Formation: α-Alkylation of Ketones with Primary Alcohols.

Miguel Peña-López1, Patrick Piehl1, Saravanakumar Elangovan1, Helfried Neumann1, Matthias Beller1.   

Abstract

A novel catalytic hydrogen-autotransfer protocol for the atom-efficient α-alkylation of ketones with readily available alcohols is presented. The use of manganese complexes bearing non-innocent PNP pincer ligands enabled the functionalization of a broad range of valuable ketones, including 2-oxindole, estrone 3-methyl ether, and testosterone. Mechanistic investigations suggest the participation of an intramolecular amidate-assisted alcohol-dehydrogenation process.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alcohols; atom economy; hydrogen transfer; ketones; manganese catalysis

Year:  2016        PMID： 27785889     DOI： 10.1002/anie.201607072

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


  13 in total

Review 1.  Direct Asymmetric Alkylation of Ketones: Still Unconquered.

Authors:  Rafael Cano; Armen Zakarian; Gerard P McGlacken
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

Review 2.  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

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.  Isoelectronic Manganese and Iron Hydrogenation/Dehydrogenation Catalysts: Similarities and Divergences.

Authors:  Nikolaus Gorgas; Karl Kirchner
Journal:  Acc Chem Res       Date:  2018-06-04       Impact factor: 22.384

5.  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

6.  Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone.

Authors:  Zhao-Feng Li; Qian Li; Li-Qing Ren; Qing-Hua Li; Yun-Gui Peng; Tang-Lin Liu
Journal:  Chem Sci       Date:  2019-05-06       Impact factor: 9.825

7.  Development and mechanistic investigation of the manganese(iii) salen-catalyzed dehydrogenation of alcohols.

Authors:  Simone V Samuelsen; Carola Santilli; Mårten S G Ahlquist; Robert Madsen
Journal:  Chem Sci       Date:  2018-11-13       Impact factor: 9.825

8.  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

9.  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

10.  Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy.

Authors:  Craig S Buxton; David C Blakemore; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336
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