Literature DB >> 19396884

Ruthenium-catalyzed selective monoamination of vicinal diols.

Sebastian Bähn1, Annegret Tillack, Sebastian Imm, Kathleen Mevius, Dirk Michalik, Dirk Hollmann, Lorenz Neubert, Matthias Beller.   

Abstract

The monoamination of vicinal diols in the presence of in situ generated ruthenium catalysts has been investigated. Among the various phosphines tested in combination with [Ru(3)(CO)(12)], N-phenyl-2-(dicyclohexyl-phosphanyl)pyrrole showed the best performance. After optimization of the reaction conditions this system was applied to different secondary amines and anilines as well as a number of vicinal diols. With the exception of ethylene glycol, monoamination of the vicinal diols occurred selectively and the corresponding amino alcohols were obtained in good yields, producing water as the only side product.

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Year:  2009        PMID： 19396884     DOI： 10.1002/cssc.200900034

Source DB:  PubMed          Journal:  ChemSusChem        ISSN： 1864-5631            Impact factor:   8.928


  8 in total

1.  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

2.  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

3.  Redox-triggered C-C coupling of diols and alkynes: synthesis of β,γ-unsaturated α-hydroxyketones and furans by ruthenium-catalyzed hydrohydroxyalkylation.

Authors:  Emma L McInturff; Khoa D Nguyen; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

4.  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

5.  Ruthenium-Catalyzed Amination of Secondary Alcohols using Borrowing Hydrogen Methodology.

Authors:  Kostiantyn O Marichev; James M Takacs
Journal:  ACS Catal       Date:  2016-02-23       Impact factor: 13.084

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.  Regioselective ruthenium catalyzed hydrohydroxyalkylation of dienes with 3-hydroxy-2-oxindoles: prenylation, geranylation, and beyond.

Authors:  Te-Yu Chen; Michael J Krische
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

8.  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
  8 in total

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