Literature DB >> 27909705

Transition metal-catalyzed iodine(iii)-mediated nitrene transfer reactions: efficient tools for challenging syntheses.

B Darses1, R Rodrigues1, L Neuville1, M Mazurais1, P Dauban1.   

Abstract

The significant progress made in the area of transition metal-catalyzed nitrene transfer into C-H or C[double bond, length as m-dash]C bonds mediated by iodine(iii) oxidants has been translated into many elegant synthetic applications. This feature article summarizes the main total syntheses that take advantage of such reactions, thereby highlighting that catalytic C(sp3)-H amination and alkene aziridination reactions have carved out their place in the organic chemist's toolbox.

Entities:  

Year:  2017        PMID: 27909705     DOI: 10.1039/c6cc07925c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  12 in total

1.  Transition-Metal- and Light-Free Directed Amination of Remote Unactivated C(sp3)-H Bonds of Alcohols.

Authors:  Daria Kurandina; Dongari Yadagiri; Mónica Rivas; Aleksei Kavun; Padon Chuentragool; Keiichi Hayama; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2019-05-08       Impact factor: 15.419

2.  Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.

Authors:  Simran Buttar; Julia Caine; Evelyne Goné; Reneé Harris; Jennifer Gillman; Roxanne Atienza; Ritu Gupta; Kimberly M Sogi; Lauren Jain; Nadia C Abascal; Yetta Levine; Lindsay M Repka; Christian M Rojas
Journal:  J Org Chem       Date:  2018-07-06       Impact factor: 4.354

3.  Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

Authors:  Logan A Combee; Shea L Johnson; Julie E Laudenschlager; Michael K Hilinski
Journal:  Org Lett       Date:  2019-03-25       Impact factor: 6.005

4.  Is the Electrophilicity of the Metal Nitrene the Sole Predictor of Metal-Mediated Nitrene Transfer to Olefins? Secondary Contributing Factors as Revealed by a Library of High-Spin Co(II) Reagents.

Authors:  Anshika Kalra; Vivek Bagchi; Patrina Paraskevopoulou; Purak Das; Lin Ai; Yiannis Sanakis; Grigorios Raptopoulos; Sudip Mohapatra; Amitava Choudhury; Zhicheng Sun; Thomas R Cundari; Pericles Stavropoulos
Journal:  Organometallics       Date:  2021-06-04       Impact factor: 3.876

5.  Visible-Light-Induced Decarboxylation of Dioxazolones to Phosphinimidic Amides and Ureas.

Authors:  Jie Pan; Haocong Li; Kai Sun; Shi Tang; Bing Yu
Journal:  Molecules       Date:  2022-06-07       Impact factor: 4.927

6.  Rhodium(ii)-catalyzed C-H aminations using N-mesyloxycarbamates: reaction pathway and by-product formation.

Authors:  Emna Azek; Maroua Khalifa; Johan Bartholoméüs; Matthias Ernzerhof; Hélène Lebel
Journal:  Chem Sci       Date:  2018-10-22       Impact factor: 9.825

7.  Uncatalyzed Oxidative C-H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study.

Authors:  Nicolaas P van Leest; Lars Grooten; Jarl Ivar van der Vlugt; Bas de Bruin
Journal:  Chemistry       Date:  2019-03-29       Impact factor: 5.236

8.  Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation.

Authors:  Alexander Fanourakis; Benjamin D Williams; Kieran J Paterson; Robert J Phipps
Journal:  J Am Chem Soc       Date:  2021-06-28       Impact factor: 15.419

Review 9.  Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis.

Authors:  Gwendal Grelier; Benjamin Darses; Philippe Dauban
Journal:  Beilstein J Org Chem       Date:  2018-06-21       Impact factor: 2.883

10.  Allylic Amination of Alkenes with Iminothianthrenes to Afford Alkyl Allylamines.

Authors:  Qiang Cheng; Junting Chen; Songyun Lin; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2020-10-01       Impact factor: 15.419

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