Literature DB >> 29989803

Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity.

Seung Wook Kim1, Thomas Wurm1, Gilmar A Brito1, Woo-Ok Jung1, Jason R Zbieg2, Craig E Stivala2, Michael J Krische1.   

Abstract

In the presence of a neutral dppf-modified iridium catalyst and Cs2CO3, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate-directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine.

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Year:  2018        PMID： 29989803      PMCID： PMC6264884          DOI： 10.1021/jacs.8b05683

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


  45 in total

1.  Ir(I)-catalyzed intermolecular regio- and enantioselective hydroamination of alkenes with heteroaromatic amines.

Authors:  Shiguang Pan; Kohei Endo; Takanori Shibata
Journal:  Org Lett       Date:  2012-01-18       Impact factor: 6.005

2.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

3.  The catalytic hydroamination of alkynes.

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

4.  Catalytic olefin hydroamination with aminium radical cations: a photoredox method for direct C-N bond formation.

Authors:  Andrew J Musacchio; Lucas Q Nguyen; G Hudson Beard; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2014-08-19       Impact factor: 15.419

5.  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

6.  Iridium-catalyzed, intermolecular hydroamination of unactivated alkenes with indoles.

Authors:  Christo S Sevov; Jianrong Steve Zhou; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-02-13       Impact factor: 15.419

7.  Coordination and organometallic chemistry of relevance to the rhodium-based catalyst for ethylene hydroamination.

Authors:  Aurélien Béthegnies; Vladislava A Kirkina; Oleg A Filippov; Jean-Claude Daran; Natalia V Belkova; Elena Shubina; Rinaldo Polic
Journal:  Inorg Chem       Date:  2011-11-14       Impact factor: 5.165

8.  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

9.  Iridium-catalyzed intermolecular hydroamination of unactivated aliphatic alkenes with amides and sulfonamides.

Authors:  Christo S Sevov; Jianrong Zhou; John F Hartwig
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419

10.  Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

Authors:  Jason G Taylor; Luis A Adrio; King Kuok Mimi Hii
Journal:  Dalton Trans       Date:  2009-12-07       Impact factor: 4.390
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  2 in total

1.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

2.  Rhodium-Catalyzed Asymmetric Hydroamination of Allyl Amines.

Authors:  Evan P Vanable; Jennifer L Kennemur; Leo A Joyce; Rebecca T Ruck; Danielle M Schultz; Kami L Hull
Journal:  J Am Chem Soc       Date:  2019-01-07       Impact factor: 15.419
  2 in total

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