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Literature DB >> 24106781

Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.

Shaolin Zhu¹, Nootaree Niljianskul, Stephen L Buchwald.

Abstract

A highly enantio- and regioselective copper-catalyzed hydroamination reaction of alkenes has been developed using diethoxymethylsilane and esters of hydroxylamines. The process tolerates a wide variety of substituted styrenes, including trans-, cis-, and β,β-disubstituted styrenes, to yield α-branched amines. In addition, aliphatic alkenes coupled to generate exclusively the anti-Markovnikov hydroamination products.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2013 PMID： 24106781 PMCID： PMC3874865 DOI： 10.1021/ja4092819

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

27 in total

1. Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

Authors: O Löber; M Kawatsura; J F Hartwig
Journal: J Am Chem Soc Date: 2001-05-09 Impact factor: 15.419

2. The catalytic hydroamination of alkynes.

Authors: René Severin; Sven Doye
Journal: Chem Soc Rev Date: 2007-03-09 Impact factor: 54.564

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. A new pathway for hydroamination. Mechanism of palladium-catalyzed addition of anilines to vinylarenes.

Authors: Ulrike Nettekoven; John F Hartwig
Journal: J Am Chem Soc Date: 2002-02-20 Impact factor: 15.419

5. Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.

Authors: Richard P Rucker; Aaron M Whittaker; Hester Dang; Gojko Lalic
Journal: J Am Chem Soc Date: 2012-04-10 Impact factor: 15.419

6. A general nickel-catalyzed hydroamination of 1,3-dienes by alkylamines: catalyst selection, scope, and mechanism.

Authors: Jan Pawlas; Yoshiaki Nakao; Motoi Kawatsura; John F Hartwig
Journal: J Am Chem Soc Date: 2002-04-10 Impact factor: 15.419

7. Regioselective and stereospecific copper-catalyzed aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines.

Authors: Naoki Matsuda; Koji Hirano; Tetsuya Satoh; Masahiro Miura
Journal: J Am Chem Soc Date: 2013-03-20 Impact factor: 15.419

8. Umpolung amination: nickel-catalyzed coupling reactions of N,N-dialkyl-N-chloroamines with diorganozinc reagents.

Authors: Timothy J Barker; Elizabeth R Jarvo
Journal: J Am Chem Soc Date: 2009-11-04 Impact factor: 15.419

9. Copper-catalyzed electrophilic amination of diorganozinc reagents.

Authors: Ashley M Berman; Jeffrey S Johnson
Journal: J Am Chem Soc Date: 2004-05-12 Impact factor: 15.419

10. Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity.

Authors: Jianrong Steve Zhou; John F Hartwig
Journal: J Am Chem Soc Date: 2008-08-21 Impact factor: 15.419

73 in total

1. Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

Authors: Sheng Guo; Jiaqi Zhu; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2020-09-11 Impact factor: 15.336

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

Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.

1. Palladium-catalyzed hydroamination of 1,3-dienes: a colorimetric assay and enantioselective additions.

2. The catalytic hydroamination of alkynes.

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

4. A new pathway for hydroamination. Mechanism of palladium-catalyzed addition of anilines to vinylarenes.

5. Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.

6. A general nickel-catalyzed hydroamination of 1,3-dienes by alkylamines: catalyst selection, scope, and mechanism.

7. Regioselective and stereospecific copper-catalyzed aminoboration of styrenes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines.

8. Umpolung amination: nickel-catalyzed coupling reactions of N,N-dialkyl-N-chloroamines with diorganozinc reagents.

9. Copper-catalyzed electrophilic amination of diorganozinc reagents.

10. Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity.

1. Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

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

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

4. Organic chemistry: One catalyst, two reactions.

5. A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination.

6. A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

7. Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

8. Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes.

9. Copper-Catalyzed Enantioselective Hydroamination of Alkenes.

10. A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.