Literature DB >> 20662536

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

Nicolaas A Vermeulen1, Jared H Delcamp, M Christina White.   

Abstract

A highly general, predictably selective C-H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (16 examples, E/Z >or= 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C-H oxidation vs C-C bond-forming methods are evaluated and discussed in four "case studies".

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Year:  2010        PMID： 20662536      PMCID： PMC3047454          DOI： 10.1021/ja104826g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  40 in total

1.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.

Authors:  Jared H Delcamp; M Christina White
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

3.  Late-stage intermolecular CH activation for lead diversification: a highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues.

Authors:  Paul A Wender; Michael K Hilinski; Alexander V W Mayweg
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

4.  Palladium(II)-Catalyzed Cyclization of Olefinic Tosylamides.

Authors:  Richard C. Larock; Timothy R. Hightower; Lisa A. Hasvold; Karl P. Peterson
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

5.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors:  Sean A Reed; M Christina White
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

6.  A stereoselective synthesis of (-)-tetrodotoxin.

Authors:  Andrew Hinman; J Du Bois
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

7.  Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

Authors:  Rodolphe Jazzar; Julien Hitce; Alice Renaudat; Julien Sofack-Kreutzer; Olivier Baudoin
Journal:  Chemistry       Date:  2010-03-01       Impact factor: 5.236

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

Authors:  Emilie Thiery; Chahinez Aouf; Julien Belloy; Dominique Harakat; Jean Le Bras; Jacques Muzart
Journal:  J Org Chem       Date:  2010-03-05       Impact factor: 4.354

9.  Catalytic allylic C-H acetoxylation and benzoyloxylation via suggested (eta(3)-allyl)palladium(IV) intermediates.

Authors:  Lukasz T Pilarski; Nicklas Selander; Dietrich Böse; Kálmán J Szabó
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

10.  Structure-based design of beta-lactamase inhibitors. 2. Synthesis and evaluation of bridged sulfactams and oxamazins.

Authors:  C Hubschwerlen; P Angehrn; K Gubernator; M G Page; J L Specklin
Journal:  J Med Chem       Date:  1998-10-08       Impact factor: 7.446
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  17 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.  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

3.  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

4.  Transmissive olefination route to putative "morinol I" lignans.

Authors:  Lihua Yao; Bhaskar Pitta; P C Ravikumar; Matthew Purzycki; Fraser F Fleming
Journal:  J Org Chem       Date:  2012-03-20       Impact factor: 4.354

5.  On the macrocyclization of the erythromycin core: preorganization is not required.

Authors:  Erik M Stang; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-27       Impact factor: 15.336

6.  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

7.  Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Heterocycles.

Authors:  Hasnain A Malik; Buck L H Taylor; John R Kerrigan; Jonathan E Grob; K N Houk; J Du Bois; Lawrence G Hamann; Andrew W Patterson
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

8.  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

9.  Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.

Authors:  Zachary C Litman; Ankit Sharma; John F Hartwig
Journal:  ACS Catal       Date:  2017-01-30       Impact factor: 13.084

10.  Terminal olefins to linear α,β-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed Wacker oxidation-dehydrogenation.

Authors:  Marinus A Bigi; M Christina White
Journal:  J Am Chem Soc       Date:  2013-05-17       Impact factor: 15.419
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