Literature DB >> 15884938

Serial ligand catalysis: a highly selective allylic C-H oxidation.

Mark S Chen1, Narayanasamy Prabagaran, Nathan A Labenz, M Christina White.   

Abstract

We are reporting a mild, chemo-, and highly regioselective Pd(II)-catalyzed allylic oxidation of alpha-olefins to furnish branched allylic esters that proceeds via a novel serial ligand catalysis mechanism in which two different ligands (i.e., vinyl sulfoxide 2 and BQ) interact sequentially with the metal to promote distinct steps of the catalytic cycle (i.e., C-H cleavage and pi-allyl functionalization, respectively).

Entities:  

Year:  2005        PMID: 15884938     DOI: 10.1021/ja0500198

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


  68 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.  Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

Authors:  Alison N Campbell; Shannon S Stahl
Journal:  Acc Chem Res       Date:  2012-01-23       Impact factor: 22.384

3.  Total synthesis of laulimalide: synthesis of the northern and southern fragments.

Authors:  Barry M Trost; W Michael Seganish; Cheol K Chung; Dominique Amans
Journal:  Chemistry       Date:  2012-02-03       Impact factor: 5.236

4.  Polyol synthesis through hydrocarbon oxidation: de novo synthesis of L-galactose.

Authors:  Dustin J Covell; Nicolaas A Vermeulen; Nathan A Labenz; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2006-12-11       Impact factor: 15.336

5.  syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.

Authors:  Kenneth J Fraunhoffer; M Christina White
Journal:  J Am Chem Soc       Date:  2007-05-22       Impact factor: 15.419

6.  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

7.  A chiral Lewis acid strategy for enantioselective allylic C-H oxidation.

Authors:  Dustin J Covell; M Christina White
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Enantioselective Total Synthesis of Nigelladine A via Late-Stage C-H Oxidation Enabled by an Engineered P450 Enzyme.

Authors:  Steven A Loskot; David K Romney; Frances H Arnold; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-07-24       Impact factor: 15.419

9.  Characterization of DMSO coordination to palladium(II) in solution and insights into the aerobic oxidation catalyst, Pd(DMSO)2(TFA)2.

Authors:  Tianning Diao; Paul White; Ilia Guzei; Shannon S Stahl
Journal:  Inorg Chem       Date:  2012-10-23       Impact factor: 5.165

10.  Illicium sesquiterpenes: divergent synthetic strategy and neurotrophic activity studies.

Authors:  Lynnie Trzoss; Jing Xu; Michelle H Lacoske; William C Mobley; Emmanuel A Theodorakis
Journal:  Chemistry       Date:  2013-03-22       Impact factor: 5.236

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