Literature DB >> 20180547

Palladium-catalyzed direct benzylation of azoles with benzyl carbonates.

Tomoya Mukai1, Koji Hirano, Tetsuya Satoh, Masahiro Miura.   

Abstract

The direct aromatic sp(2) C-H benzylation of azole compounds with benzyl carbonates proceeds efficiently in the presence of a Pd(2)(dba)(3)/dppp catalyst system and NaOAc as a base to afford the corresponding diarylmethanes in good yields. In addition, the same palladium catalyst enables the direct benzylic sp(3) C-H benzylation with the second benzyl carbonates without employing any external base.

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Year:  2010        PMID: 20180547     DOI: 10.1021/ol1002576

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

Review 1.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

2.  Palladium-catalyzed C3-benzylation of indoles.

Authors:  Ye Zhu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

3.  Decarboxylative benzylations of alkynes and ketones.

Authors:  Robert R P Torregrosa; Yamuna Ariyarathna; Kalicharan Chattopadhyay; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

4.  Iron-catalyzed heterocycle and arene deprotonative alkylation.

Authors:  Ly Dieu Tran; Olafs Daugulis
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

5.  Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Authors:  Kalicharan Cattopadhyay; Antonio Recio; Jon A Tunge
Journal:  Org Biomol Chem       Date:  2012-07-25       Impact factor: 3.876

6.  Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles.

Authors:  Kalicharan Chattopadhyay; Erik Fenster; Alexander J Grenning; Jon A Tunge
Journal:  Beilstein J Org Chem       Date:  2012-07-27       Impact factor: 2.883

7.  Additive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles.

Authors:  Marko Kljajic; Johannes G Puschnig; Hansjörg Weber; Rolf Breinbauer
Journal:  Org Lett       Date:  2016-12-12       Impact factor: 6.005

Review 8.  Benzylic Methylene Functionalizations of Diarylmethanes.

Authors:  Upma Gulati; Radhika Gandhi; Joydev K Laha
Journal:  Chem Asian J       Date:  2020-09-09
  8 in total

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