Literature DB >> 24156560

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

Boyoung Y Park1, T Patrick Montgomery, Victoria J Garza, Michael J Krische.   

Abstract

Heteroaromatic secondary alcohols react with isoprene to form products of hydrohydroxyalkylation in the presence of ruthenium(0) catalysts generated from Ru3(CO)12 and tricyclohexylphosphine, enabling direct conversion of secondary to tertiary alcohols in the absence of premetalated reagents or stoichiometric byproducts. The putative oxaruthenacycle intermediate has been isolated and characterized, and reversible metallacycle formation has been demonstrated.

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Year:  2013        PMID： 24156560      PMCID： PMC3855325          DOI： 10.1021/ja4087193

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


  21 in total

1.  Rhodium-catalyzed coupling reactions of arylboronic acids to olefins in aqueous media.

Authors:  M Lautens; A Roy; K Fukuoka; K Fagnou; B Martín-Matute
Journal:  J Am Chem Soc       Date:  2001-06-06       Impact factor: 15.419

2.  Enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylheteroarenes.

Authors:  Graham Pattison; Guillaume Piraux; Hon Wai Lam
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

Review 3.  Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation.

Authors:  Seung Hwan Cho; Ji Young Kim; Jaesung Kwak; Sukbok Chang
Journal:  Chem Soc Rev       Date:  2011-06-06       Impact factor: 54.564

4.  Synthesis of α-amino acid amides: ruthenium-catalyzed amination of α-hydroxy amides.

Authors:  Min Zhang; Sebastian Imm; Sebastian Bähn; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-10       Impact factor: 15.336

5.  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

6.  Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand.

Authors:  Mark Lautens; Masahiro Yoshida
Journal:  Org Lett       Date:  2002-01-10       Impact factor: 6.005

7.  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

8.  Ruthenium-catalyzed selective monoamination of vicinal diols.

Authors:  Sebastian Bähn; Annegret Tillack; Sebastian Imm; Kathleen Mevius; Dirk Michalik; Dirk Hollmann; Lorenz Neubert; Matthias Beller
Journal:  ChemSusChem       Date:  2009       Impact factor: 8.928

9.  Rhodium-catalyzed addition of arylboronic acids to alkynyl aza-heteroaromatic compounds in water.

Authors:  Mark Lautens; Masahiro Yoshida
Journal:  J Org Chem       Date:  2003-02-07       Impact factor: 4.354

10.  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
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  29 in total

1.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

Review 2.  Engaging Aldehydes in CuH-Catalyzed Reductive Coupling Reactions: Stereoselective Allylation with Unactivated 1,3-Diene Pronucleophiles.

Authors:  Chengxi Li; Kwangmin Shin; Richard Y Liu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

3.  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

4.  Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

Authors:  Xiao-Hui Yang; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-08-09       Impact factor: 15.419

5.  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

6.  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 7.  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

Review 8.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors:  Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal:  Top Curr Chem (Cham)       Date:  2016-05-30

9.  Enantioselective Coupling of Dienes and Phosphine Oxides.

Authors:  Shao-Zhen Nie; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-11-19       Impact factor: 15.419

Review 10.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336
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