Literature DB >> 24039135

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

Zachary K Wickens1, Bill Morandi, Robert H Grubbs.   

Abstract

Breaking the rules: Reversal of the high Markovnikov selectivity of Wacker-type oxidations was accomplished using a nitrite co-catalyst. Unbiased aliphatic alkenes can be oxidized with high yield and aldehyde selectivity, and several functional groups are tolerated. (18) O-labeling experiments indicate that the aldehydic O atom is derived from the nitrite salt.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; anti-Markovnikov; oxidation; oxygen; palladium

Year:  2013        PMID： 24039135     DOI： 10.1002/anie.201306756

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

1.  Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite.

Authors:  Zachary K Wickens; Pablo E Guzmán; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-06       Impact factor: 15.336

2.  Late-Stage Diversification: A Motivating Force in Organic Synthesis.

Authors:  Kelly E Kim; Alexia N Kim; Carter J McCormick; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2021-10-06       Impact factor: 16.383

3.  Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

Authors:  Jiaming Li; Robert H Grubbs; Brian M Stoltz
Journal:  Org Lett       Date:  2016-10-18       Impact factor: 6.005

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

Authors:  Ryan J DeLuca; Jennifer L Edwards; Laura D Steffens; Brian W Michel; Xiaoxiao Qiao; Chunyin Zhu; Silas P Cook; Matthew S Sigman
Journal:  J Org Chem       Date:  2013-02-06       Impact factor: 4.354

5.  Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

Authors:  Crystal K Chu; Daniel T Ziegler; Brian Carr; Zachary K Wickens; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-25       Impact factor: 15.336

6.  Picking Flowers with Carbon Nanotube Sensors.

Authors:  Sean I Hwang; Alexander Star
Journal:  ACS Cent Sci       Date:  2020-04-03       Impact factor: 14.553

7.  Trace Ethylene Sensing via Wacker Oxidation.

Authors:  Darryl Fong; Shao-Xiong Luo; Rafaela S Andre; Timothy M Swager
Journal:  ACS Cent Sci       Date:  2020-03-18       Impact factor: 14.553

8.  The formyloxyl radical: electrophilicity, C-H bond activation and anti-Markovnikov selectivity in the oxidation of aliphatic alkenes.

Authors:  Miriam Somekh; Mark A Iron; Alexander M Khenkin; Ronny Neumann
Journal:  Chem Sci       Date:  2020-10-02       Impact factor: 9.825

9.  The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

Authors:  Christopher E Reimann; Aurapat Ngamnithiporn; Kohei Hayashida; Daisuke Saito; Katerina M Korch; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-06       Impact factor: 16.823

10.  Catalytic Isohypsic-Redox Sequences for the Rapid Generation of Csp3 -Containing Heterocycles.

Authors:  Craig D Smith; David Phillips; Alina Tirla; David J France
Journal:  Chemistry       Date:  2018-11-02       Impact factor: 5.236
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