Literature DB >> 23768239

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

Tien M Nguyen1, David A Nicewicz.   

Abstract

Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium tetrafluoroborate and thiophenol as a hydrogen-atom donor furnished the nitrogen-containing heterocycles with complete regiocontrol. Two examples of intermolecular anti-Markovnikov alkene hydroamination are also disclosed.

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Year:  2013        PMID： 23768239      PMCID： PMC3754854          DOI： 10.1021/ja4031616

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


  51 in total

1.  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

2.  Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates.

Authors:  Xiaoqing Han; Ross A Widenhoefer
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-03       Impact factor: 15.336

Review 3.  Hydroamination: direct addition of amines to alkenes and alkynes.

Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
Journal:  Chem Rev       Date:  2008-08-26       Impact factor: 60.622

4.  Catalytic, enantioselective intramolecular hydroamination of primary amines tethered to di- and trisubstituted alkenes.

Authors:  Yulia Chapurina; Houssein Ibrahim; Régis Guillot; Emilie Kolodziej; Jacqueline Collin; Alexander Trifonov; Emmanuelle Schulz; Jérôme Hannedouche
Journal:  J Org Chem       Date:  2011-11-22       Impact factor: 4.354

5.  Mechanistic Studies of Ruthenium-Catalyzed Anti-Markovnikov Hydroamination of Vinylarenes: Intermediates and Evidence for Catalysis through pi-Arene Complexes.

Authors:  Jun Takaya; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

6.  Eosin Y catalyzed visible light oxidative C-C and C-P bond formation.

Authors:  Durga Prasad Hari; Burkhard König
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

7.  Intramolecular hydroamination of unbiased and functionalized primary aminoalkenes catalyzed by a rhodium aminophosphine complex.

Authors:  Lisa D Julian; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

8.  Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

Authors:  Chunhui Dai; Francesco Meschini; Jagan M R Narayanam; Corey R J Stephenson
Journal:  J Org Chem       Date:  2012-04-18       Impact factor: 4.354

9.  Heavier alkaline earth catalysts for the intermolecular hydroamination of vinylarenes, dienes, and alkynes.

Authors:  Christine Brinkmann; Anthony G M Barrett; Michael S Hill; Panayiotis A Procopiou
Journal:  J Am Chem Soc       Date:  2012-01-18       Impact factor: 15.419

10.  Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines.

Authors:  Hai-Chao Xu; Kevin D Moeller
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419
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  46 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.  Direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes.

Authors:  Andrew J Perkowski; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2013-07-03       Impact factor: 15.419

5.  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

6.  Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines.

Authors:  David C Miller; Jacob M Ganley; Andrew J Musacchio; Trevor C Sherwood; William R Ewing; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2019-10-14       Impact factor: 15.419

7.  Formal Anti-Markovnikov Hydroamination of Terminal Olefins.

Authors:  Sarah M Bronner; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-01       Impact factor: 9.825

8.  PCET-Enabled Olefin Hydroamidation Reactions with N-Alkyl Amides.

Authors:  Suong T Nguyen; Qilei Zhu; Robert R Knowles
Journal:  ACS Catal       Date:  2019-04-17       Impact factor: 13.084

Review 9.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

10.  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
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