Literature DB >> 22519742

Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source.

Quyen Nguyen1, Ke Sun, Tom G Driver.   

Abstract

Rhodium(II) dicarboxylate complexes were discovered to catalyze the intramolecular amination of unactivated primary, secondary, or tertiary aliphatic C-H bonds using aryl azides as the N-atom precursor. While a strong electron-withdrawing group on the nitrogen atom is typically required to achieve this reaction, we found that both electron-rich and electron-poor aryl azides are efficient sources for the metal nitrene reactive intermediate.
© 2012 American Chemical Society

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Year:  2012        PMID: 22519742      PMCID: PMC3397916          DOI: 10.1021/ja301519q

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


  44 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.  A DFT study on the mechanism of Rh2(II,II)-catalyzed intramolecular amidation of carbamates.

Authors:  Xufeng Lin; Cunyuan Zhao; Chi-Ming Che; Zhuofeng Ke; David Lee Phillips
Journal:  Chem Asian J       Date:  2007-09-03

3.  Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

Authors:  Erika Milczek; Nadège Boudet; Simon Blakey
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  A diruthenium catalyst for selective, intramolecular allylic C-H amination: reaction development and mechanistic insight gained through experiment and theory.

Authors:  Mark Edwin Harvey; Djamaladdin G Musaev; J Du Bois
Journal:  J Am Chem Soc       Date:  2011-10-07       Impact factor: 15.419

5.  Copper and silver complexes containing organic azide ligands: syntheses, structures, and theoretical investigation of [HB(3,5-(CF3)2Pz)3]CuNNN(1-Ad) and [HB(3,5-(CF3)2Pz)3]AgN(1-Ad)NN (where Pz = pyrazolyl and 1-Ad = 1-adamantyl).

Authors:  H V Dias; S A Polach; S K Goh; E F Archibong; D S Marynick
Journal:  Inorg Chem       Date:  2000-08-21       Impact factor: 5.165

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

Authors:  Tom G Driver
Journal:  Org Biomol Chem       Date:  2010-07-08       Impact factor: 3.876

7.  Catalytic C-H bond amination from high-spin iron imido complexes.

Authors:  Evan R King; Elisabeth T Hennessy; Theodore A Betley
Journal:  J Am Chem Soc       Date:  2011-03-15       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.  C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide.

Authors:  Paul A Vadola; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2009-11-18       Impact factor: 15.419

10.  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
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  19 in total

1.  Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors:  Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2015-07-07       Impact factor: 15.419

2.  C-H activation: the road less travelled to amination.

Authors:  Olga V Zatolochnaya; Vladimir Gevorgyan
Journal:  Nat Chem       Date:  2014-08       Impact factor: 24.427

3.  Quantum Suppression of Intramolecular Deuterium Kinetic Isotope Effects in a Pericyclic Hydrogen Transfer Reaction.

Authors:  Xiao Li; Darrin M York; Matthew P Meyer
Journal:  J Phys Chem A       Date:  2019-04-22       Impact factor: 2.781

4.  Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins Using Nonactivated N Atom Precursors.

Authors:  Tianning Deng; Wrickban Mazumdar; Yuki Yoshinaga; Pooja B Patel; Dana Malo; Tala Malo; Donald J Wink; Tom G Driver
Journal:  J Am Chem Soc       Date:  2021-11-08       Impact factor: 15.419

5.  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

6.  Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

Authors:  Quyen Nguyen; Tuyen Nguyen; Tom G Driver
Journal:  J Am Chem Soc       Date:  2013-01-03       Impact factor: 15.419

7.  Palladium(0)-catalyzed Heck reaction/C-H activation/amination sequence with diaziridinone: a facile approach to indolines.

Authors:  Huaiji Zheng; Yingguang Zhu; Yian Shi
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

8.  Triiodide-Mediated δ-Amination of Secondary C-H Bonds.

Authors:  Ethan A Wappes; Stacy C Fosu; Trevor C Chopko; David A Nagib
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-07       Impact factor: 15.336

9.  Rh2(II)-catalyzed selective aminomethylene migration from styryl azides.

Authors:  Chen Kong; Navendu Jana; Tom G Driver
Journal:  Org Lett       Date:  2013-02-04       Impact factor: 6.005

10.  Development of a Suzuki cross-coupling reaction between 2-azidoarylboronic pinacolate esters and vinyl triflates to enable the synthesis of [2,3]-fused indole heterocycles.

Authors:  Navendu Jana; Quyen Nguyen; Tom G Driver
Journal:  J Org Chem       Date:  2014-03-12       Impact factor: 4.354

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