Literature DB >> 10840948

The electrophilic amination of carbanions: an unconventional new entry to C-N bond formation

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Abstract

The electrophilic amination of carbanions allows the preparation of a wide range of amines through an unconventional C-N bond-forming reaction. The concepts behind the varied synthetic approaches, classified by the nature of the aminating agent and of the organometallic species, are discussed. The mild operational conditions, the high selectivity, and the availability of the starting materials are good assets of these processes which nicely complement each other. New appealing and flexible routes can be devised, leading in several cases to the synthesis of otherwise not easily accessible N-containing compounds.

Entities:  

Year:  2000        PMID: 10840948     DOI: 10.1002/(sici)1521-3765(20000417)6:8<1281::aid-chem1281>3.0.co;2-f

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  9 in total

1.  Enantioselective alpha-amination of 1,3-dicarbonyl compounds using squaramide derivatives as hydrogen bonding catalysts.

Authors:  Hideyuki Konishi; Tin Yiu Lam; Jeremiah P Malerich; Viresh H Rawal
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

Review 2.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

3.  Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents.

Authors:  Minh H Nguyen; Amos B Smith
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

4.  An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

Authors:  Zhishi Ye; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

5.  Copper-Catalyzed Electrophilic Amination of Heteroaromatic and Aromatic C-H Bonds via TMPZnCl•LiCl Mediated Metalation.

Authors:  Stacey L McDonald; Charles E Hendrick; Katie J Bitting; Qiu Wang
Journal:  Organic Synth       Date:  2015-11-17

6.  Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades.

Authors:  Lucrezia Angelini; Jacob Davies; Marco Simonetti; Laia Malet Sanz; Nadeem S Sheikh; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-12       Impact factor: 15.336

7.  Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Authors:  Timothy J Donohoe; Christopher R Jones; Anne F Kornahrens; Luiz C A Barbosa; Louise J Walport; Matthew R Tatton; Michael O'Hagan; Akshat H Rathi; David B Baker
Journal:  J Org Chem       Date:  2013-12-12       Impact factor: 4.354

8.  Azaphilic versus Carbophilic Coupling at C=N Bonds: Key Steps in Titanium-Assisted Multicomponent Reactions.

Authors:  Torsten Roth; Hubert Wadepohl; Eric Clot; Lutz H Gade
Journal:  Chemistry       Date:  2015-11-06       Impact factor: 5.236

Review 9.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823

  9 in total

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