Directed C-H Bond Oxidation of Bridged Cycloalkanes Catalyzed by Palladium(II) Acetate

Chemistry : a European Journal
Marta LarrosaRadim Hrdina

Abstract

We have developed a synthesis of 1,2-substituted adamantane carboxylic acids and further bridged cycloalkanes (cage compounds) by palladium acetate-catalyzed C-H bond oxidation. Acetoxylation of cycloalkane framework was performed using picolylamide as a directing group. Modification of the substrate, ligand design and variation of reaction conditions enabled us to study the mechanism of acetoxylation of aliphatic compounds. Post-functionalization reactions and cleavage of the directing group were developed. For the first time the synthesis and characterization of a β-C3 -tri-substituted adamantane derivatives was achieved.

References

Jul 1, 1990·Journal of Medicinal Chemistry·P S ManchandI S Sim
Apr 24, 2004·The Journal of Organic Chemistry·Yong FengQing-Xiang Guo
Aug 5, 2004·Journal of the American Chemical Society·Lopa V DesaiMelanie S Sanford
Dec 18, 2007·Angewandte Chemie·Hartmut SchwertfegerPeter R Schreiner
Jan 13, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·P K Sajith, Cherumuttathu H Suresh
Jan 30, 2010·Chemical Society Reviews·Ling-Min XuZhang-Jie Shi
Feb 11, 2010·Chemical Reviews·Petr SehnalIan J S Fairlamb
Sep 17, 2010·Journal of the American Chemical Society·Qiang ZhangJohn A Porco
Jul 7, 2012·Organic Letters·Raja K RitAkhila K Sahoo
Feb 26, 2013·Chemical Reviews·Lukas WankaPeter R Schreiner
Oct 11, 2013·The Journal of Organic Chemistry·Long JuYuhong Zhang
Nov 18, 2014·Angewandte Chemie·Jeffrey Y W MakCraig M Williams
Jan 22, 2015·Chemical Communications : Chem Comm·Meining WangAo Zhang
May 27, 2015·Marine Drugs·Mohamed Elamir F HegazyPaul W Paré
Jul 15, 2015·Chemical Society Reviews·Tegan P Stockdale, Craig M Williams
Aug 4, 2015·Angewandte Chemie·Elizabeth H Krenske, Craig M Williams
Aug 27, 2015·Chemical Communications : Chem Comm·Jiantao HuYu Rao
Mar 24, 2016·Angewandte Chemie·Zhongxing HuangGuangbin Dong
Apr 14, 2016·Chemical Society Reviews·T GenschJ Wencel-Delord
Feb 9, 2017·Journal of the American Chemical Society·Qi-Liang YangTian-Sheng Mei
Mar 16, 2017·Chemical Reviews·Zachary G BrillThomas J Maimone
Apr 6, 2017·Chemical Reviews·Franck Le BideauFrançoise Dumas
Oct 19, 2017·Angewandte Chemie·Volodymyr KozelGünter Haufe
Oct 21, 2017·Chemical Society Reviews·Mélanie M LorionLutz Ackermann
Dec 23, 2017·Organic Letters·Anuska ShresthaMelanie S Sanford

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Citations

Jul 22, 2018·Chemistry : a European Journal·Jonathan BeckerSiegfried Schindler
Nov 5, 2019·The Journal of Organic Chemistry·Yumeela Ganga-SahAndrew J Bennet

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