Literature DB >> 24764195

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

Tien M Nguyen1, Namita Manohar, David A Nicewicz.   

Abstract

Disclosed herein is a general catalytic system for the intermolecular anti-Markovnikov hydroamination of alkenes. By using an organocatalytic photoredox system, α- and β-substituted styrenes as well as aliphatic alkenes undergo anti-Markovnikov hydroamination. Heterocyclic amines were also successfully employed as nitrogen nucleophiles, thus providing a direct route to heterocyclic motifs common in medicinal agents.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; amines; organocatalysis; photochemistry; radicals

Mesh：

Substances：

Year:  2014        PMID： 24764195      PMCID： PMC4073672          DOI： 10.1002/anie.201402443

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


  24 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

Review 2.  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

3.  Heavier group 2 metals and intermolecular hydroamination: a computational and synthetic assessment.

Authors:  Anthony G M Barrett; Christine Brinkmann; Mark R Crimmin; Michael S Hill; Patricia Hunt; Panayiotis A Procopiou
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

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.  A chiral phenoxyamine magnesium catalyst for the enantioselective hydroamination/cyclization of aminoalkenes and intermolecular hydroamination of vinyl arenes.

Authors:  Xiaoming Zhang; Thomas J Emge; Kai C Hultzsch
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-09       Impact factor: 15.336

6.  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

7.  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

8.  Redox-photosensitized aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia.

Authors:  Masahide Yasuda; Ryuji Kojima; Hiroshi Tsutsui; Daigo Utsunomiya; Kazuaki Ishii; Koutaro Jinnouchi; Tsutomu Shiragami; Toshiaki Yamashita
Journal:  J Org Chem       Date:  2003-10-03       Impact factor: 4.354

9.  Efficient and regioselective synthesis of 2-alkyl-2H-indazoles.

Authors:  Mui Cheung; Amogh Boloor; Jeffrey A Stafford
Journal:  J Org Chem       Date:  2003-05-16       Impact factor: 4.354

10.  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
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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.  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

3.  Catalytic Strategy for Regioselective Arylethylamine Synthesis.

Authors:  Allyson J Boyington; Ciaran P Seath; Avery M Zearfoss; Zihao Xu; Nathan T Jui
Journal:  J Am Chem Soc       Date:  2019-02-21       Impact factor: 15.419

4.  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

5.  Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

Authors:  Qilei Zhu; David E Graff; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2018-01-04       Impact factor: 15.419

Review 6.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

7.  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

8.  Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.

Authors:  Casey B Roos; Joachim Demaerel; David E Graff; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2020-03-20       Impact factor: 15.419

9.  Mechanistically Guided Design of Ligands That Significantly Improve the Efficiency of CuH-Catalyzed Hydroamination Reactions.

Authors:  Andy A Thomas; Klaus Speck; Ilia Kevlishvili; Zhaohong Lu; Peng Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-10-15       Impact factor: 15.419

10.  Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols.

Authors:  Stephanie G E Amos; Stefano Nicolai; Jerome Waser
Journal:  Chem Sci       Date:  2020-09-22       Impact factor: 9.825
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