Literature DB >> 28387054

Domino N-/C-Arylation via In Situ Generation of a Directing Group: Atom-Efficient Arylation Using Diaryliodonium Salts.

Christopher J Teskey1, Shariar M A Sohel1, Danielle L Bunting1, Sachin G Modha1, Michael F Greaney1.   

Abstract

Both aryl components of diaryliodonium salts can be used in a domino one-pot reaction via in situ generation of a directing group. A number of heterocycles undergo N-arylation which is followed by ruthenium-catalyzed C-arylation. Notably the reaction extends well to unsymmetrical diaryliodonium salts with a number of highly selective examples shown.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C-H activation; N-heterocycles; arylation; iodonium compounds

Year:  2017        PMID： 28387054     DOI： 10.1002/anie.201701523

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

1.  Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium-Catalyzed C-H Bond Functionalization Methodology.

Authors:  Se Hun Kwak; Nurbey Gulia; Olafs Daugulis
Journal:  J Org Chem       Date:  2018-05-08       Impact factor: 4.354

2.  Stereoselective Direct N-Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent.

Authors:  János T Csenki; Ádám Mészáros; Zsombor Gonda; Zoltán Novák
Journal:  Chemistry       Date:  2021-10-06       Impact factor: 5.020

Review 3.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

4.  Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions.

Authors:  Haiwen Wang; Liyun Liang; Zhirong Guo; Hui Peng; Shuang Qiao; Nemai Saha; Daqian Zhu; Wenbin Zeng; Yunyun Chen; Peng Huang; Shijun Wen
Journal:  iScience       Date:  2020-06-23

Review 5.  Atom-economical group-transfer reactions with hypervalent iodine compounds.

Authors:  Andreas Boelke; Peter Finkbeiner; Boris J Nachtsheim
Journal:  Beilstein J Org Chem       Date:  2018-05-30       Impact factor: 2.883

6.  DFT calculations on the mechanism of copper-catalysed tandem arylation-cyclisation reactions of alkynes and diaryliodonium salts.

Authors:  Tamás Károly Stenczel; Ádám Sinai; Zoltán Novák; András Stirling
Journal:  Beilstein J Org Chem       Date:  2018-07-12       Impact factor: 2.883

7.  Cu(OTf)2 -Mediated Cross-Coupling of Nitriles and N-Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products*.

Authors:  Nicola L Bell; Chao Xu; James W B Fyfe; Julien C Vantourout; Jeremy Brals; Sonia Chabbra; Bela E Bode; David B Cordes; Alexandra M Z Slawin; Thomas M McGuire; Allan J B Watson
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336

8.  Cobalt-catalyzed, directed arylation of C-H bonds in N-aryl pyrazoles.

Authors:  Tung T Nguyen; Lam V Le; Hai H Pham; Dung H Nguyen; Nam T S Phan; Ha V Le; Anh N Q Phan
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

9.  Copper-catalyzed O-alkenylation of phosphonates.

Authors:  Nuria Vázquez-Galiñanes; Mariña Andón-Rodríguez; Patricia Gómez-Roibás; Martín Fañanás-Mastral
Journal:  Beilstein J Org Chem       Date:  2020-04-03       Impact factor: 2.883

10.  Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives.

Authors:  Dae-Kwon Kim; Hyun-Suk Um; Hoyoon Park; Seonwoo Kim; Jin Choi; Chulbom Lee
Journal:  Chem Sci       Date:  2020-10-22       Impact factor: 9.825
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