Literature DB >> 21953742

Regio- and chemoselective metalation of arenes and heteroarenes using hindered metal amide bases.

Benjamin Haag1, Marc Mosrin, Hiriyakkanavar Ila, Vladimir Malakhov, Paul Knochel.   

Abstract

The preparation of highly functionalized organometallic compounds can be achieved by direct C-H activation of a broad range of unsaturated substrates using lithium chloride solubilized 2,2,6,6-tetramethylpiperidide bases (TMP(n)MX(m)⋅p LiCl). These are excellent reagents for converting a wide range of aromatic and heterocyclic substrates into valuable organometallic reagents with broad applications in organic synthesis.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21953742     DOI： 10.1002/anie.201101960

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


  30 in total

1.  Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Arene Metalations.

Authors:  Russell F Algera; Yun Ma; David B Collum
Journal:  J Am Chem Soc       Date:  2017-10-16       Impact factor: 15.419

2.  Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation.

Authors:  David Huang; Yizhou Zhao; Timothy R Newhouse
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

3.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

4.  New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds.

Authors:  Milad Mesgar; Justin Nguyen-Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2018-10-10       Impact factor: 15.419

5.  Mild and general conditions for negishi cross-coupling enabled by the use of palladacycle precatalysts.

Authors:  Yang Yang; Nathan J Oldenhuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-22       Impact factor: 15.336

6.  Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.

Authors:  Stacey L McDonald; Charles E Hendrick; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-25       Impact factor: 15.336

7.  Azine Activation via Silylium Catalysis.

Authors:  Carla Obradors; Benjamin List
Journal:  J Am Chem Soc       Date:  2021-04-28       Impact factor: 15.419

8.  (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.

Authors:  Johannes H Harenberg; Niels Weidmann; Alexander J Wiegand; Carla A Hoefer; Rajasekar Reddy Annapureddy; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-03       Impact factor: 15.336

9.  A regioselectively 1,1',3,3'-tetrazincated ferrocene complex displaying core and peripheral reactivity.

Authors:  Gordon W Honeyman; David R Armstrong; William Clegg; Eva Hevia; Alan R Kennedy; Ross McLellan; Samantha A Orr; John A Parkinson; Donna L Ramsay; Stuart D Robertson; Stephen Towie; Robert E Mulvey
Journal:  Chem Sci       Date:  2020-03-27       Impact factor: 9.825

10.  Photocatalytic redox-neutral hydroxyalkylation of N-heteroaromatics with aldehydes.

Authors:  Hiromu Fuse; Hiroyasu Nakao; Yutaka Saga; Arisa Fukatsu; Mio Kondo; Shigeyuki Masaoka; Harunobu Mitsunuma; Motomu Kanai
Journal:  Chem Sci       Date:  2020-10-12       Impact factor: 9.825
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