Literature DB >> 22860983

Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: application to the preparation of natural flavones and isoflavones.

Lydia Klier1, Tomke Bresser, Tobias A Nigst, Konstantin Karaghiosoff, Paul Knochel.   

Abstract

A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl(2), a C(3) zincation is observed, whereas in the presence of MgCl(2) or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22860983     DOI： 10.1021/ja306178q

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


  9 in total

1.  Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors.

Authors:  Jeffrey C Holder; Alexander N Marziale; Michele Gatti; Bin Mao; Brian M Stoltz
Journal:  Chemistry       Date:  2012-12-03       Impact factor: 5.236

2.  An efficient strategy to syntheses of isoflavones.

Authors:  Longzhu Liu; Qiuya Wang; Zunting Zhang; Qiong Zhang; Zichao Du; Dong Xue; Tingting Wang
Journal:  Mol Divers       Date:  2014-08-03       Impact factor: 2.943

3.  Synthesis of isoflavones by room-temperature nickel-catalyzed cross-couplings of 3-iodo(bromo)chromones with arylzincs.

Authors:  Zunting Zhang; Jinfeng Qiao; Ding Wang; Ling Han; Ru Ding
Journal:  Mol Divers       Date:  2014-01-29       Impact factor: 2.943

4.  Functionalised Mn(VI)-nanoparticles: an advanced high-valent magnetic catalyst.

Authors:  Saikat Khamarui; Yasmin Saima; Radha M Laha; Subhadeep Ghosh; Dilip K Maiti
Journal:  Sci Rep       Date:  2015-03-02       Impact factor: 4.379

5.  Selective Functionalization of Tetrathiafulvalene Using Mg- and Zn-TMP-Bases: Preparation of Mono-, Di-, Tri-, and Tetrasubstituted Derivatives.

Authors:  Julia Nafe; Florian Auras; Konstantin Karaghiosoff; Thomas Bein; Paul Knochel
Journal:  Org Lett       Date:  2015-10-15       Impact factor: 6.005

Review 6.  Advances in the site-selective C-5, C-3 and C-2 functionalization of chromones via sp2 C-H activation.

Authors:  Anjitha Theres Benny; Ethiraj Kannatt Radhakrishnan
Journal:  RSC Adv       Date:  2022-01-26       Impact factor: 3.361

7.  Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

Authors:  Alexander Kremsmair; Andreas Hess; Benjamin Heinz; Paul Knochel
Journal:  Chemistry       Date:  2021-11-29       Impact factor: 5.020

8.  Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications.

Authors:  Shekinah A Bass; Dynasty M Parker; Tania J Bellinger; Aireal S Eaton; Angelica S Dibble; Kaata L Koroma; Sylvia A Sekyi; David A Pollard; Fenghai Guo
Journal:  Molecules       Date:  2018-07-15       Impact factor: 4.411

9.  A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl⋅LiCl.

Authors:  Moritz Balkenhohl; Harish Jangra; Ilya S Makarov; Shu-Mei Yang; Hendrik Zipse; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 16.823
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.