Literature DB >> 20617243

Recent advances in transition metal-catalyzed N-atom transfer reactions of azides.

Tom G Driver1.   

Abstract

Transitn class="Chemical">ion metal-catalyzed N-atom transfer reactions of azides provide efficient ways to construct new carbon-nitrogen and sulfur-nitrogen bonds. These reactions are inherently green: no additive besides catalyst is needed to form the nitrenoid reactive intermediate, and the by-product of the reaction is environmentally benign N(2) gas. As such, azides can be useful precursors for transition metal-catalyzed N-atom transfer to sulfides, olefins and C-H bonds. These methods offer competitive selectivities and comparable substrate scope as alternative processes to generate metal nitrenoids.

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Year:  2010        PMID: 20617243      PMCID: PMC3095841          DOI: 10.1039/c005219c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  49 in total

Review 1.  Kinetics, spectroscopy, and computational chemistry of arylnitrenes.

Authors:  N P Gritsan; M S Platz
Journal:  Chem Rev       Date:  2006-09       Impact factor: 60.622

2.  Cobalt(II)-catalyzed intramolecular C-H amination with phosphoryl azides: formation of 6- and 7-membered cyclophosphoramidates.

Authors:  Hongjian Lu; Jingran Tao; Jess E Jones; Lukasz Wojtas; X Peter Zhang
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

3.  Fe(II)-catalyzed imidation of allyl sulfides and subsequent

Authors: 
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

4.  Cobalt-catalyzed intermolecular C-H amination with bromamine-T as nitrene source.

Authors:  Jeremiah D Harden; Joshua V Ruppel; Guang-Yao Gao; X Peter Zhang
Journal:  Chem Commun (Camb)       Date:  2007-09-03       Impact factor: 6.222

5.  Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

Authors:  Benjamin J Stokes; Brankica Jovanović; Huijun Dong; Kathleen J Richert; Ryan D Riell; Tom G Driver
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

6.  Simple conversion of aromatic amines into azides.

Authors:  Qi Liu; Yitzhak Tor
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

7.  Study of the chemistry of ortho- and para-biphenylnitrenes by laser flash photolysis and time-resolved IR experiments and by B3LYP and CASPT2 calculations.

Authors:  Meng-Lin Tsao; Nina Gritsan; Tammi R James; Matthew S Platz; David A Hrovat; Weston Thatcher Borden
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

8.  Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors:  Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal:  J Am Chem Soc       Date:  2007-12-12       Impact factor: 15.419

9.  Construction of robust ruthenium(salen)(CO) complexes and asymmetric aziridination with nitrene precursors in the form of azide compounds that bear easily removable N-sulfonyl groups.

Authors:  Hirotoshi Kawabata; Kazufumi Omura; Tatsuya Uchida; Tsutomu Katsuki
Journal:  Chem Asian J       Date:  2007-02-05

10.  Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement.

Authors:  Masakazu Murakami; Tatsuya Uchida; Bunnai Saito; Tsutomu Katsuki
Journal:  Chirality       Date:  2003-02       Impact factor: 2.437

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  46 in total

1.  Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; synthesis of dimebolin.

Authors:  Huijun Dong; Regina T Latka; Tom G Driver
Journal:  Org Lett       Date:  2011-04-25       Impact factor: 6.005

2.  C-H bond functionalization: An aminated reaction.

Authors:  Tom G Driver
Journal:  Nat Chem       Date:  2013-09       Impact factor: 24.427

3.  Arene C-H amination at nickel in terphenyl-diphosphine complexes with labile metal-arene interactions.

Authors:  David E Herbert; Nadia C Lara; Theodor Agapie
Journal:  Chemistry       Date:  2013-10-14       Impact factor: 5.236

4.  Characterization of Porphyrin-Co(III)-'Nitrene Radical' Species Relevant in Catalytic Nitrene Transfer Reactions.

Authors:  Monalisa Goswami; Volodymyr Lyaskovskyy; Sérgio R Domingos; Wybren Jan Buma; Sander Woutersen; Oliver Troeppner; Ivana Ivanović-Burmazović; Hongjian Lu; Xin Cui; X Peter Zhang; Edward J Reijerse; Serena DeBeer; Matti M van Schooneveld; Florian Felix Pfaff; Kallol Ray; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2015-04-16       Impact factor: 15.419

Review 5.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

6.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

7.  I(III)-Catalyzed Oxidative Cyclization-Migration Tandem Reactions of Unactivated Anilines.

Authors:  Tianning Deng; Emily Shi; Elana Thomas; Tom G Driver
Journal:  Org Lett       Date:  2020-10-30       Impact factor: 6.005

8.  Effective synthesis of chiral N-fluoroaryl aziridines through enantioselective aziridination of alkenes with fluoroaryl azides.

Authors:  Li-Mei Jin; Xue Xu; Hongjian Lu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-15       Impact factor: 15.336

9.  Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

Authors:  Pericles Stavropoulos
Journal:  Comments Mod Chem A Comments Inorg Chem       Date:  2016-04-29       Impact factor: 4.533

10.  Spin-Selective Generation of Triplet Nitrenes: Olefin Aziridination through Visible-Light Photosensitization of Azidoformates.

Authors:  Spencer O Scholz; Elliot P Farney; Sangyun Kim; Desiree M Bates; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-06       Impact factor: 15.336

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