Literature DB >> 23808532

Direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes.

Andrew J Perkowski1, David A Nicewicz.   

Abstract

A direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes is reported. The catalyst system is comprised of the Fukuzumi acridinium photooxidant (1) and a substoichiometric quantity of a hydrogen-atom donor. Oxidizable olefins, such as styrenes, trisubstituted aliphatic alkenes, and enamides, can be employed along with a variety of carboxylic acids to afford the anti-Markovnikov addition adducts exclusively. A deuterium-labeling experiment lends insight to the potential mechanism.

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Year:  2013        PMID: 23808532      PMCID: PMC3757928          DOI: 10.1021/ja4057294

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

1.  Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: recent developments and trends.

Authors:  Matthias Beller; Jayasree Seayad; Annegret Tillack; Haijun Jiao
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

2.  Electron-transfer state of 9-mesityl-10-methylacridinium ion with a much longer lifetime and higher energy than that of the natural photosynthetic reaction center.

Authors:  Shunichi Fukuzumi; Hiroaki Kotani; Kei Ohkubo; Seiji Ogo; Nikolai V Tkachenko; Helge Lemmetyinen
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

3.  Gold(I)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins.

Authors:  Cai-Guang Yang; Chuan He
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

4.  Electrophilicity and nucleophilicity index for radicals.

Authors:  Freija De Vleeschouwer; Veronique Van Speybroeck; Michel Waroquier; Paul Geerlings; Frank De Proft
Journal:  Org Lett       Date:  2007-06-09       Impact factor: 6.005

5.  Synthesis of highly substituted tetrahydrofurans by catalytic polar-radical-crossover cycloadditions of alkenes and alkenols.

Authors:  Jean-Marc M Grandjean; David A Nicewicz
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-25       Impact factor: 15.336

6.  Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

Authors:  Zigang Li; Junliang Zhang; Chad Brouwer; Cai-Guang Yang; Nicholas W Reich; Chuan He
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

7.  Ruthenium catalyzed addition reaction of carboxylic acid across olefins without beta-hydride elimination.

Authors:  Yohei Oe; Tetsuo Ohta; Yoshihiko Ito
Journal:  Chem Commun (Camb)       Date:  2004-06-15       Impact factor: 6.222

8.  Iron-catalysed green synthesis of carboxylic esters by the intermolecular addition of carboxylic acids to alkenes.

Authors:  Jun-Chul Choi; Kazufumi Kohno; Daisuke Masuda; Hiroyuki Yasuda; Toshiyasu Sakakura
Journal:  Chem Commun (Camb)       Date:  2008-02-14       Impact factor: 6.222

9.  Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

Authors:  Tien M Nguyen; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2013-06-19       Impact factor: 15.419

10.  Direct catalytic anti-markovnikov hydroetherification of alkenols.

Authors:  David S Hamilton; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2012-11-05       Impact factor: 15.419

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  26 in total

1.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

2.  Organic Photoredox Catalysis as a General Strategy for Anti-Markovnikov Alkene Hydrofunctionalization.

Authors:  David A Nicewicz; David S Hamilton
Journal:  Synlett       Date:  2014-03-05       Impact factor: 2.454

3.  anti-Markovnikov hydroamination of alkenes catalyzed by a two-component organic photoredox system: direct access to phenethylamine derivatives.

Authors:  Tien M Nguyen; Namita Manohar; David A Nicewicz
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-24       Impact factor: 15.336

4.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

5.  A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis.

Authors:  Kaila A Margrey; William L Czaplyski; David A Nicewicz; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2018-03-16       Impact factor: 15.419

6.  Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.

Authors:  Shishi Lin; Shane D Lies; Christopher S Gravatt; Tehshik P Yoon
Journal:  Org Lett       Date:  2016-12-29       Impact factor: 6.005

7.  Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles.

Authors:  Loïc R E Pantaine; John A Milligan; Jennifer K Matsui; Christopher B Kelly; Gary A Molander
Journal:  Org Lett       Date:  2019-03-12       Impact factor: 6.005

8.  Anti-Markovnikov Hydroazidation of Activated Olefins via Organic Photoredox Catalysis.

Authors:  Nicholas P R Onuska; Megan E Schutzbach-Horton; José L Rosario Collazo; David A Nicewicz
Journal:  Synlett       Date:  2019-09-24       Impact factor: 2.454

9.  The direct anti-Markovnikov addition of mineral acids to styrenes.

Authors:  Dale J Wilger; Jean-Marc M Grandjean; Taylor R Lammert; David A Nicewicz
Journal:  Nat Chem       Date:  2014-07-13       Impact factor: 24.427

10.  Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.

Authors:  Nicholas L Reed; Grace A Lutovsky; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2021-04-15       Impact factor: 15.419

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