Literature DB >> 31745374

A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation.

Tanner C Jankins1, Ziyang Qin1, Keary M Engle1.   

Abstract

This manuscript describes a modular method for preparing N-alkyl phosphinic amides from primary or secondary alcohols and primary phosphinic amide (R1R2P=ONH2) nucleophiles via transfer hydrogenation. The transformation typically proceeds in excellent yields, employs conveniently available reagents, and produces water as the only byproduct.

Entities:  

Keywords:  Amination; Phosphinic Amide; Phosphorous; Ruthenium; Transfer Hydrogenation

Year:  2019        PMID： 31745374      PMCID： PMC6863173          DOI： 10.1016/j.tet.2019.04.029

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  20 in total

1.  Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System.

Authors:  Tian Zeng; Zhen Liu; Michael A Schmidt; Martin D Eastgate; Keary M Engle
Journal:  Org Lett       Date:  2018-06-11       Impact factor: 6.005

Review 2.  The golden age of transfer hydrogenation.

Authors:  Dong Wang; Didier Astruc
Journal:  Chem Rev       Date:  2015-06-10       Impact factor: 60.622

3.  Bond activation and catalysis by ruthenium pincer complexes.

Authors:  Chidambaram Gunanathan; David Milstein
Journal:  Chem Rev       Date:  2014-11-14       Impact factor: 60.622

4.  Pd(II)-catalyzed enantioselective synthesis of P-stereogenic phosphinamides via desymmetric C-H arylation.

Authors:  Zhi-Jun Du; Jing Guan; Guo-Jie Wu; Peng Xu; Lian-Xun Gao; Fu-She Han
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

5.  Three-component synthesis of alpha,beta-cyclopropyl-gamma-amino acids.

Authors:  Peter Wipf; Corey R J Stephenson
Journal:  Org Lett       Date:  2005-03-17       Impact factor: 6.005

6.  Chiral bidentate aminophosphine ligands: synthesis, coordination chemistry and asymmetric catalysis.

Authors:  Eric J Zijp; Jarl Ivar van der Vlugt; Duncan M Tooke; Anthony L Spek; Dieter Vogt
Journal:  Dalton Trans       Date:  2005-01-04       Impact factor: 4.390

7.  Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation.

Authors:  Zhen Liu; Yanyan Wang; Zichen Wang; Tian Zeng; Peng Liu; Keary M Engle
Journal:  J Am Chem Soc       Date:  2017-08-04       Impact factor: 15.419

8.  Unlocking P(V): Reagents for chiral phosphorothioate synthesis.

Authors:  Kyle W Knouse; Justine N deGruyter; Michael A Schmidt; Bin Zheng; Julien C Vantourout; Cian Kingston; Stephen E Mercer; Ivar M Mcdonald; Richard E Olson; Ye Zhu; Chao Hang; Jason Zhu; Changxia Yuan; Qinggang Wang; Peter Park; Martin D Eastgate; Phil S Baran
Journal:  Science       Date:  2018-08-02       Impact factor: 47.728

9.  Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation.

Authors:  John A Gurak; Kin S Yang; Zhen Liu; Keary M Engle
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419

10.  From racemic alcohols to enantiopure amines: Ru-catalyzed diastereoselective amination.

Authors:  Nathan J Oldenhuis; Vy M Dong; Zhibin Guan
Journal:  J Am Chem Soc       Date:  2014-08-29       Impact factor: 15.419
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  1 in total

1.  Absolute Configuration and Conformation of (-)-R-t-Butylphenylphosphinoamidate: Chiroptical Spectroscopy and X-ray Analysis.

Authors:  Ana G Petrovic; Prasad L Polavarapu; Andrzej Łopusiński; Dorota Krasowska; Wanda Wieczorek; Małgorzata Szyrej; Jarosław Błaszczyk; Józef Drabowicz
Journal:  J Org Chem       Date:  2020-08-19       Impact factor: 4.354
  1 in total

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