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Literature DB >> 22469028

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

Richard P Rucker¹, Aaron M Whittaker, Hester Dang, Gojko Lalic.

Abstract

A method for highly selective anti-Markovnikov hydroamination of terminal alkenes is reported. The one-pot procedure involves hydroboration of the alkene followed by a novel electrophilic amination of the alkyl borane catalyzed by an NHC-Cu complex. Terminal alkenes are successfully transformed into tertiary alkyl amines in the presence of a variety of functional groups in yields ranging from 80 to 97% with excellent regioselectivity. Results of a preliminary study of the reaction mechanism are also described.

Entities: Chemical

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Year: 2012 PMID： 22469028 DOI： 10.1021/ja3023829

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

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Cited

30 in total

1. 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

9. Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.

Authors: Cheng Zhang; C James Chou
Journal: Org Lett Date: 2016-10-19 Impact factor: 6.005

10. Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

Authors: Steven A Rossi; Kirk W Shimkin; Qun Xu; Luis M Mori-Quiroz; Donald A Watson
Journal: Org Lett Date: 2013-04-23 Impact factor: 6.005

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

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

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

3. Transition-metal free umpolung carbon-nitrogen vs. carbon-chlorine bond formation.

4. Mechanistic studies of copper(I)-catalyzed 1,3-halogen migration.

5. Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters.

6. Formal Anti-Markovnikov Hydroamination of Terminal Olefins.

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

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

9. Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor.

10. Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.