Literature DB >> 24852383

Copper-catalyzed esterification of alkylbenzenes with cyclic ethers and cycloalkanes via C(sp3)-H activation following cross-dehydrogenative coupling.

Saroj Kumar Rout1, Srimanta Guin, Wajid Ali, Anupal Gogoi, Bhisma K Patel.   

Abstract

A copper-catalyzed cross-dehydrogenative coupling strategy has been developed for the synthesis of two classes of esters from simple solvents. The reaction of methylarenes with cyclic ethers resulted in α-acyloxy ethers involving four sp(3) C-H cleavages, while treatment of methylarenes with cycloalkanes led to the formation of allyl esters at the expense of six consecutive sp(3) C-H bonds.

Entities:  

Year:  2014        PMID: 24852383     DOI: 10.1021/ol5011906

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


  6 in total

1.  Chemo- and regioselective benzylic C(sp3)-H oxidation bridging the gap between hetero- and homogeneous copper catalysis.

Authors:  Shantanu Nandi; Shuvam Mondal; Ranjan Jana
Journal:  iScience       Date:  2022-05-02

2.  Copper-catalyzed oxidative dehydrogenative carboxylation of unactivated alkanes to allylic esters via alkenes.

Authors:  Ba L Tran; Matthias Driess; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-11-24       Impact factor: 15.419

Review 3.  Cross-dehydrogenative coupling for the intermolecular C-O bond formation.

Authors:  Igor B Krylov; Vera A Vil'; Alexander O Terent'ev
Journal:  Beilstein J Org Chem       Date:  2015-01-20       Impact factor: 2.883

4.  TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides.

Authors:  Cui Chen; Weibing Liu; Peng Zhou
Journal:  Beilstein J Org Chem       Date:  2016-10-25       Impact factor: 2.883

5.  PdII-Catalyzed Oxidative Aldehyde-sp2C-H Functionalization and Cyclization Using NHC with Mild Oxidant DMSO for the Selective Synthesis of Esters, Sugar-Based Analogues, and β-Hydroxy Chromanones: An 18O-Labeling Study.

Authors:  Satinath Sarkar; Radha M Laha; Rajendra N Mitra; Dilip K Maiti
Journal:  ACS Omega       Date:  2016-11-21

6.  Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones.

Authors:  Ping Qian; Bingnan Du; Wei Jiao; Haibo Mei; Jianlin Han; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2016-02-17       Impact factor: 2.883

  6 in total

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