Literature DB >> 20141222

Palladium-catalyzed allylic acyloxylation of terminal alkenes in the presence of a base.

Emilie Thiery1, Chahinez Aouf, Julien Belloy, Dominique Harakat, Jean Le Bras, Jacques Muzart.   

Abstract

The efficiency and the selectivity of the Pd-catalyzed oxidation, in carboxylic acids, of terminal alkenes are strongly improved in the presence of a base. The methodology is particularly well adapted for the oxidation of homoallylic alcohols, for which the resulting acyloxylated products are obtained selectively as E-isomers in fair to good yields.

Entities:  

Year:  2010        PMID： 20141222     DOI： 10.1021/jo902587u

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


  13 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.  Diversification of a β-Lactam Pharmacophore via Allylic C-H Amination: Accelerating Effect of Lewis Acid Co-Catalyst.

Authors:  Xiangbing Ben Qi; Grant T Rice; Manjinder S Lall; Mark S Plummer; M Christina White
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

3.  O2-Promoted Allylic Acetoxylation of Alkenes: Assessment of "Push" vs. "Pull" Mechanisms and Comparison between O2 and Benzoquinone.

Authors:  Tianning Diao; Shannon S Stahl
Journal:  Polyhedron       Date:  2014-12-14       Impact factor: 3.052

4.  Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.

Authors:  Chao Jiang; Dustin J Covell; Antonia F Stepan; Mark S Plummer; M Christina White
Journal:  Org Lett       Date:  2012-02-24       Impact factor: 6.005

5.  Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C-H Acetoxylation Catalyzed by Pd(OAc)2/4,5-Diazafluoren-9-one.

Authors:  Jonathan N Jaworski; Caitlin V Kozack; Stephen J Tereniak; Spring Melody M Knapp; Clark R Landis; Jeffrey T Miller; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2019-06-25       Impact factor: 15.419

6.  Enantioselective functionalization of allylic C-H bonds following a strategy of functionalization and diversification.

Authors:  Ankit Sharma; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-11-14       Impact factor: 15.419

7.  Catalyst-controlled C-O versus C-N allylic functionalization of terminal olefins.

Authors:  Iulia I Strambeanu; M Christina White
Journal:  J Am Chem Soc       Date:  2013-07-31       Impact factor: 15.419

8.  Synthesis of complex allylic esters via C-H oxidation vs C-C bond formation.

Authors:  Nicolaas A Vermeulen; Jared H Delcamp; M Christina White
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

9.  Benzoquinone Cocatalyst Contributions to DAF/Pd(OAc)2-Catalyzed Aerobic Allylic Acetoxylation in the Absence and Presence of a Co(salophen) Cocatalyst.

Authors:  Caitlin V Kozack; Stephen J Tereniak; Jonathan N Jaworski; Bao Li; David L Bruns; Spring M M Knapp; Clark R Landis; Shannon S Stahl
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.700

10.  A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.

Authors:  Dustin J Covell; M Christina White
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457
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