Literature DB >> 20222741

Transition-metal-free electrophilic amination between aryl Grignard reagents and N-chloroamines.

Takuji Hatakeyama1, Yuya Yoshimoto, Sujit K Ghorai, Masaharu Nakamura.   

Abstract

In the presence of N,N,N',N'-tetramethylethylenediamine (TMEDA) as an additive, easily prepared and handled N-chloroamines react with aryl Grignard reagents to give a variety of arylamines in good to excellent yields. Functional groups such as ester and nitrile are compatible under the reaction conditions.

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Year:  2010        PMID: 20222741     DOI: 10.1021/ol100235b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

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

Authors:  John J Sirois; Brenton DeBoef
Journal:  Tetrahedron Lett       Date:  2015-10-07       Impact factor: 2.415

2.  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

3.  Combining organometallic reagents, the sulfur dioxide surrogate DABSO, and amines: a one-pot preparation of sulfonamides, amenable to array synthesis.

Authors:  Alex S Deeming; Claire J Russell; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

4.  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

5.  Stereoretentive Pd-catalyzed Kumada-Corriu couplings of alkenyl halides at room temperature.

Authors:  Arkady L Krasovskiy; Stephen Haley; Karl Voigtritter; Bruce H Lipshutz
Journal:  Org Lett       Date:  2014-08-07       Impact factor: 6.005

6.  Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime.

Authors:  Chunling Yuan; Lei Zhang; Yingdai Zhao
Journal:  Molecules       Date:  2019-11-18       Impact factor: 4.411

  6 in total

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