Literature DB >> 28164712

Ruthenium(0)-Catalyzed C-C Coupling of Alkynes and 3-Hydroxy-2-oxindoles: Direct C-H Vinylation of Alcohols.

Tom Luong1, Shujie Chen1, Ke Qu1, Emma L McInturff1, Michael J Krische1.   

Abstract

Upon exposure to a ruthenium(0) catalyst, N-benzyl-3-hydroxy-2-oxindoles react with diverse alkynes to form products of C-H vinylation with complete control of regioselectivity and olefin geometry. This method contributes to a growing body of catalytic processes that enable direct conversion of lower alcohols to higher alcohols in the absence of stoichiometric organometallic reagents.

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Year:  2017        PMID： 28164712      PMCID： PMC5651673          DOI： 10.1021/acs.orglett.7b00174

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  21 in total

1.  Diastereo- and enantioselective iridium-catalyzed carbonyl propargylation from the alcohol or aldehyde oxidation level: 1,3-enynes as allenylmetal equivalents.

Authors:  Laina M Geary; Sang Kook Woo; Joyce C Leung; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-15       Impact factor: 15.336

2.  A Metallacycle Fragmentation Strategy for Vinyl Transfer from Enol Carboxylates to Secondary Alcohol C-H Bonds via Osmium- or Ruthenium-Catalyzed Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

3.  Dirhodium(II) tetrakis[methyl 2-oxaazetidine-4-carboxylate]: a chiral dirhodium(II) carboxamidate of exceptional reactivity and selectivity.

Authors:  M P Doyle; S B Davies; W Hu
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

4.  Regio- and diastereoselective C-C coupling of α-olefins and styrenes to 3-hydroxy-2-oxindoles by Ru-catalyzed hydrohydroxyalkylation.

Authors:  Eiji Yamaguchi; Jeffrey Mowat; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-05       Impact factor: 15.336

5.  Ruthenium catalyzed hydrohydroxyalkylation of isoprene with heteroaromatic secondary alcohols: isolation and reversible formation of the putative metallacycle intermediate.

Authors:  Boyoung Y Park; T Patrick Montgomery; Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-10-24       Impact factor: 15.419

Review 6.  Spirooxindoles: Promising scaffolds for anticancer agents.

Authors:  Bin Yu; De-Quan Yu; Hong-Min Liu
Journal:  Eur J Med Chem       Date:  2014-06-27       Impact factor: 6.514

7.  Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-04-29       Impact factor: 15.419

8.  Direct, redox-neutral prenylation and geranylation of secondary carbinol C-H bonds: C4-regioselectivity in ruthenium-catalyzed C-C couplings of dienes to α-hydroxy esters.

Authors:  Joyce C Leung; Laina M Geary; Te-Yu Chen; Jason R Zbieg; Michael J Krische
Journal:  J Am Chem Soc       Date:  2012-09-17       Impact factor: 15.419

9.  Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences.

Authors:  Benito Alcaide; Pedro Almendros; Raquel Rodríguez-Acebes
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354

10.  Ruthenium-catalyzed hydrohydroxyalkylation of acrylates with diols and α-hydroxycarbonyl compounds to form spiro- and α-methylene-γ-butyrolactones.

Authors:  Emma L McInturff; Jeffrey Mowat; Andrew R Waldeck; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-11-05       Impact factor: 15.419
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  4 in total

1.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
Journal:  J Org Chem       Date:  2017-12-08       Impact factor: 4.354

2.  Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct.

Authors:  Richard Y Liu; Yujing Zhou; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-02-01       Impact factor: 15.419

3.  Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.

Authors:  Marvin Kischkewitz; Bruno Marinic; Nicolas Kratena; Yonglin Lai; Hamish B Hepburn; Mark Dow; Kirsten E Christensen; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-13       Impact factor: 16.823

Review 4.  Acetylene in Organic Synthesis: Recent Progress and New Uses.

Authors:  Vladimir V Voronin; Maria S Ledovskaya; Alexander S Bogachenkov; Konstantin S Rodygin; Valentine P Ananikov
Journal:  Molecules       Date:  2018-09-24       Impact factor: 4.411
  4 in total

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