Literature DB >> 21615149

Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts.

Tue B Petersen1, Rehan Khan, Berit Olofsson.   

Abstract

An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates. The transition-metal-free conditions are compatible with a range of functional groups, and good chemoselectivity is observed with unsymmetric diaryliodonium salts. Furthermore, steric hindrance in the ortho positions is well tolerated both in the carboxylic acid and in the diaryliodonium salt, yielding aryl esters that cannot be obtained via other esterification protocols.

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Year:  2011        PMID: 21615149     DOI: 10.1021/ol2012082

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


  11 in total

1.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Authors:  Andrii Monastyrskyi; Niranjan K Namelikonda; Roman Manetsch
Journal:  J Org Chem       Date:  2015-02-24       Impact factor: 4.354

2.  Direct Radiofluorination of Arene C-H Bonds via Photoredox Catalysis Using a Peroxide as the Terminal Oxidant.

Authors:  Li Wang; Alexander R White; Wei Chen; Zhanhong Wu; David A Nicewicz; Zibo Li
Journal:  Org Lett       Date:  2020-10-01       Impact factor: 6.005

3.  Decarbonylative organoboron cross-coupling of esters by nickel catalysis.

Authors:  Kei Muto; Junichiro Yamaguchi; Djamaladdin G Musaev; Kenichiro Itami
Journal:  Nat Commun       Date:  2015-06-29       Impact factor: 14.919

4.  C-H arylation of triphenylene, naphthalene and related arenes using Pd/C.

Authors:  Karl D Collins; Roman Honeker; Suhelen Vásquez-Céspedes; Dan-Tam D Tang; Frank Glorius
Journal:  Chem Sci       Date:  2014-12-22       Impact factor: 9.825

5.  One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8.

Authors:  Teppei Sasaki; Katsuhiko Moriyama; Hideo Togo
Journal:  Beilstein J Org Chem       Date:  2018-02-05       Impact factor: 2.883

6.  Highly Reactive Cyclic Monoaryl Iodoniums Tuned as Carbene Generators Couple with Nucleophiles under Metal-Free Conditions.

Authors:  Haiwen Wang; Liyun Liang; Zhirong Guo; Hui Peng; Shuang Qiao; Nemai Saha; Daqian Zhu; Wenbin Zeng; Yunyun Chen; Peng Huang; Shijun Wen
Journal:  iScience       Date:  2020-06-23

7.  Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts.

Authors:  Gabriella Kervefors; Leonard Kersting; Berit Olofsson
Journal:  Chemistry       Date:  2021-03-03       Impact factor: 5.236

8.  Arylation with unsymmetrical diaryliodonium salts: a chemoselectivity study.

Authors:  Joel Malmgren; Stefano Santoro; Nazli Jalalian; Fahmi Himo; Berit Olofsson
Journal:  Chemistry       Date:  2013-06-20       Impact factor: 5.236

9.  Room temperature, metal-free arylation of aliphatic alcohols.

Authors:  Raju Ghosh; Erik Lindstedt; Nazli Jalalian; Berit Olofsson
Journal:  ChemistryOpen       Date:  2014-04-11       Impact factor: 2.911

10.  Sterically Congested 2,6-Disubstituted Anilines from Direct C-N Bond Formation at an Iodine(III) Center.

Authors:  Nicola Lucchetti; Michelangelo Scalone; Serena Fantasia; Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

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