Literature DB >> 23678959

Sterically controlled, palladium-catalyzed intermolecular amination of arenes.

Ruja Shrestha1, Paramita Mukherjee, Yichen Tan, Zachary C Litman, John F Hartwig.   

Abstract

We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc)2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.

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Year:  2013        PMID: 23678959     DOI: 10.1021/ja4032677

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


  26 in total

1.  Pd-catalyzed aryl C-H imidation with arene as the limiting reagent.

Authors:  Gregory B Boursalian; Ming-Yu Ngai; Katarzyna N Hojczyk; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2013-09-03       Impact factor: 15.419

2.  Regioselective C-H bond amination by aminoiodanes.

Authors:  Abhishek A Kantak; Louis Marchetti; Brenton DeBoef
Journal:  Chem Commun (Camb)       Date:  2015-02-28       Impact factor: 6.222

3.  Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

Authors:  Kyle Clagg; Haiyun Hou; Adam B Weinstein; David Russell; Shannon S Stahl; Stefan G Koenig
Journal:  Org Lett       Date:  2016-07-12       Impact factor: 6.005

4.  Non-directed aromatic C-H amination: catalytic and mechanistic studies enabled by Pd catalyst and reagent design.

Authors:  H M D Bandara; D Jin; M A Mantell; K D Field; A Wang; R P Narayanan; N A Deskins; M H Emmert
Journal:  Catal Sci Technol       Date:  2016-03-24       Impact factor: 6.119

5.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

6.  Dirhodium-catalyzed C-H arene amination using hydroxylamines.

Authors:  Mahesh P Paudyal; Adeniyi Michael Adebesin; Scott R Burt; Daniel H Ess; Zhiwei Ma; László Kürti; John R Falck
Journal:  Science       Date:  2016-09-09       Impact factor: 47.728

7.  A Strategy to Aminate Pyridines, Diazines, and Pharmaceuticals via Heterocyclic Phosphonium Salts.

Authors:  Chirag Patel; Margaret Mohnike; Michael C Hilton; Andrew McNally
Journal:  Org Lett       Date:  2018-04-17       Impact factor: 6.005

8.  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

9.  Ligand-accelerated non-directed C-H functionalization of arenes.

Authors:  Peng Wang; Pritha Verma; Guoqin Xia; Jun Shi; Jennifer X Qiao; Shiwei Tao; Peter T W Cheng; Michael A Poss; Marcus E Farmer; Kap-Sun Yeung; Jin-Quan Yu
Journal:  Nature       Date:  2017-11-22       Impact factor: 49.962

10.  A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp(2) C-H Bond Amination.

Authors:  James Roane; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2016-03-18       Impact factor: 15.419

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