Literature DB >> 23363387

Wacker-type oxidation of internal alkenes using Pd(Quinox) and TBHP.

Ryan J DeLuca1, Jennifer L Edwards, Laura D Steffens, Brian W Michel, Xiaoxiao Qiao, Chunyin Zhu, Silas P Cook, Matthew S Sigman.   

Abstract

The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.

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Year:  2013        PMID： 23363387      PMCID： PMC3615722          DOI： 10.1021/jo302638v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  18 in total

1.  Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

Authors:  Alison N Campbell; Paul B White; Ilia A Guzei; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-11-03       Impact factor: 15.419

2.  Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation.

Authors:  M J Gaunt; J Yu; J B Spencer
Journal:  Chem Commun (Camb)       Date:  2001-09-21       Impact factor: 6.222

3.  Wacker-type oxidation of internal olefins using a PdCl2/N,N-dimethylacetamide catalyst system under copper-free reaction conditions.

Authors:  Takato Mitsudome; Keiichi Mizumoto; Tomoo Mizugaki; Koichiro Jitsukawa; Kiyotomi Kaneda
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-08       Impact factor: 15.336

4.  The mechanism of the Wacker reaction: a tale of two hydroxypalladations.

Authors:  John A Keith; Patrick M Henry
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands.

Authors:  Brian W Michel; Laura D Steffens; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-05-09       Impact factor: 15.419

6.  An unexpected oxidation of unactivated methylene C-H using DIB/TBHP protocol.

Authors:  Yi Zhao; Wai-Leung Yim; Chong Kiat Tan; Ying-Yeung Yeung
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

7.  Catalyst-controlled Wacker-type oxidation of protected allylic amines.

Authors:  Brian W Michel; Jessica R McCombs; Andrea Winkler; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

8.  Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-Panaxytriol and (R)- and (S)-Falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered cascade reaction.

Authors:  Sandra F Mayer; Andreas Steinreiber; Romano V A Orru; Kurt Faber
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

9.  A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant: application to classically challenging substrates.

Authors:  Brian W Michel; Andrew M Camelio; Candace N Cornell; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2009-05-06       Impact factor: 15.419

10.  Aldehyde-selective Wacker-type oxidation of unbiased alkenes enabled by a nitrite co-catalyst.

Authors:  Zachary K Wickens; Bill Morandi; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-13       Impact factor: 15.336
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  6 in total

Review 1.  Allylic azides: synthesis, reactivity, and the Winstein rearrangement.

Authors:  Angela S Carlson; Joseph J Topczewski
Journal:  Org Biomol Chem       Date:  2019-05-08       Impact factor: 3.876

2.  Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.

Authors:  Hsin-Chun Chiu; Xin Yi See; Ian A Tonks
Journal:  ACS Catal       Date:  2018-11-29       Impact factor: 13.084

3.  Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins.

Authors:  Jawahar L Jat; Mahesh P Paudyal; Hongyin Gao; Qing-Long Xu; Muhammed Yousufuddin; Deepa Devarajan; Daniel H Ess; László Kürti; John R Falck
Journal:  Science       Date:  2014-01-03       Impact factor: 47.728

4.  Regiocontrolled Wacker Oxidation of Cinnamyl Azides.

Authors:  Angela S Carlson; Cristian Calcanas; Ryan M Brunner; Joseph J Topczewski
Journal:  Org Lett       Date:  2018-03-02       Impact factor: 6.005

5.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

6.  Selective Wacker type oxidation of a macrocyclic diene to the corresponding monounsaturated ketone used as fragrance.

Authors:  Tom Brunzel; Johannes Heppekausen; Johannes Panten; Angela Köckritz
Journal:  RSC Adv       Date:  2019-09-04       Impact factor: 3.361
  6 in total

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