Literature DB >> 25364496

A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Kun Liu1, M Todd Hovey1, Karl A Scheidt1.   

Abstract

N-heterocyclic carbenes (NHC) have been extensively studied as organocatalysts and ligands for transition metals, but the successful integration of NHCs and late transition metals in cooperative catalysis remains an underexplored area. We have developed a cooperative palladium-catalyzed allylation of NHC-activated aldehydes to access a variety of 3-allyl dihydrocoumarin derivatives. Kinetic experiments support a cooperative pathway for this transformation.

Entities:  

Year:  2014        PMID： 25364496      PMCID： PMC4212655          DOI： 10.1039/C4SC01536C

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  49 in total

1.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

3.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

Review 4.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

5.  Enantioselective formation of substituted 3,4-dihydrocoumarins by a multicatalytic one-pot process.

Authors:  Christian Borch Jacobsen; Łukasz Albrecht; Jonas Udmark; Karl Anker Jørgensen
Journal:  Org Lett       Date:  2012-10-17       Impact factor: 6.005

6.  Cooperative catalysis through noncovalent interactions.

Authors:  Weijun Tang; Steven Johnston; Jonathan A Iggo; Neil G Berry; Marie Phelan; Luyun Lian; John Bacsa; Jianliang Xiao
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-03       Impact factor: 15.336

7.  A palladium/chiral amine co-catalyzed enantioselective dynamic cascade reaction: synthesis of polysubstituted carbocycles with a quaternary carbon stereocenter.

Authors:  Guangning Ma; Samson Afewerki; Luca Deiana; Carlos Palo-Nieto; Leifeng Liu; Junliang Sun; Ismail Ibrahem; Armando Córdova
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-25       Impact factor: 15.336

8.  Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a net C-H insertion.

Authors:  Barry M Trost; F Dean Toste; Kevin Greenman
Journal:  J Am Chem Soc       Date:  2003-04-16       Impact factor: 15.419

9.  N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors:  Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

10.  Chiral magnesium(II) binaphtholates as cooperative Brønsted/Lewis acid-base catalysts for the highly enantioselective addition of phosphorus nucleophiles to α,β-unsaturated esters and ketones.

Authors:  Manabu Hatano; Takahiro Horibe; Kazuaki Ishihara
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-13       Impact factor: 15.336
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  5 in total

1.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

2.  N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors:  Dian-Feng Chen; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2016-11-18       Impact factor: 3.157

3.  Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.

Authors:  Anna V Davies; Keegan P Fitzpatrick; Rick C Betori; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

4.  Highly selective palladium-benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions.

Authors:  Antonio Monopoli; Pietro Cotugno; Carlo Giorgio Zambonin; Francesco Ciminale; Angelo Nacci
Journal:  Beilstein J Org Chem       Date:  2015-06-10       Impact factor: 2.883

5.  Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes.

Authors:  You-Feng Han; Ying Huang; Hao Liu; Zhong-Hua Gao; Chun-Lin Zhang; Song Ye
Journal:  Nat Commun       Date:  2022-09-30       Impact factor: 17.694
  5 in total

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