Literature DB >> 26066660

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

Boyoung Y Park1, Tom Luong1, Hiroki Sato1, Michael J Krische1.   

Abstract

A strategy for catalytic vinyl transfer from enol carboxylates to activated secondary alcohol C-H bonds is described. Using XPhos-modified ruthenium(0) or osmium(0) complexes, enol carboxylate-carbonyl oxidative coupling forms transient β-acyloxy-oxametallacycles, which eliminate carboxylate to deliver allylic ruthenium(II) or osmium(II) alkoxides. Reduction of the metal(II) salt via hydrogen transfer from the secondary alcohol reactant releases the product of carbinol C-H vinylation and regenerates ketone and zero-valent catalyst.

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Year:  2015        PMID： 26066660      PMCID： PMC4481174          DOI： 10.1021/jacs.5b04688

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


  31 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

2.  Coupling reactions of zirconocene complexes and heterosubstituted alkenes.

Authors:  José Barluenga; Félix Rodríguez; Lucía Alvarez-Rodrigo; Francisco J Fañanás
Journal:  Chem Soc Rev       Date:  2005-07-20       Impact factor: 54.564

3.  Nickel-catalyzed redox-economical coupling of alcohols and alkynes to form allylic alcohols.

Authors:  Kenichiro Nakai; Yuji Yoshida; Takuya Kurahashi; Seijiro Matsubara
Journal:  J Am Chem Soc       Date:  2014-05-20       Impact factor: 15.419

4.  Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.

Authors:  Abbas Hassan; Michael J Krische
Journal:  Org Process Res Dev       Date:  2011-11-18       Impact factor: 3.317

5.  Direct vinylation of alcohols or aldehydes employing alkynes as vinyl donors: a ruthenium catalyzed C-C bond-forming transfer hydrogenation.

Authors:  Ryan L Patman; Mani Raj Chaulagain; Vanessa M Williams; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

6.  Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels.

Authors:  Laina M Geary; Ben W Glasspoole; Mary M Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2013-02-28       Impact factor: 15.419

7.  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

8.  Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.

Authors:  Soo Bong Han; Jong Rock Kong; Michael J Krische
Journal:  Org Lett       Date:  2008-08-26       Impact factor: 6.005

9.  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

10.  An annulation reaction for the synthesis of cross-conjugated triene-containing hydroindanes from acyclic precursors.

Authors:  Xiayun Cheng; Glenn C Micalizio
Journal:  Org Lett       Date:  2014-09-12       Impact factor: 6.005
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  6 in total

1.  Osmium(0)-Catalyzed C-C Coupling of Ethylene and α-Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation.

Authors:  Boyoung Y Park; Tom Luong; Hiroki Sato; Michael J Krische
Journal:  J Org Chem       Date:  2016-09-08       Impact factor: 4.354

2.  Diols as Dienophiles: Bridged Carbocycles via Ruthenium(0)-Catalyzed Transfer Hydrogenative Cycloadditions of Cyclohexadiene or Norbornadiene.

Authors:  Hiroki Sato; Keisuke Fukaya; Binit Sharma Poudel; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-10       Impact factor: 15.336

Review 3.  Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.

Authors:  Khoa D Nguyen; Boyoung Y Park; Tom Luong; Hiroki Sato; Victoria J Garza; Michael J Krische
Journal:  Science       Date:  2016-10-21       Impact factor: 47.728

4.  Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides.

Authors:  Matthias Bender; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  Science       Date:  2017-08-25       Impact factor: 47.728

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

Authors:  Tom Luong; Shujie Chen; Ke Qu; Emma L McInturff; Michael J Krische
Journal:  Org Lett       Date:  2017-02-06       Impact factor: 6.005

6.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       Impact factor: 15.336
  6 in total

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