Literature DB >> 26032920

Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.

Nathaniel H Park1, Ekaterina V Vinogradova1, David S Surry1, Stephen L Buchwald2.   

Abstract

In Pd-catalyzed C-N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed to suppress undesired side reactions often encountered when these amine nucleophiles are used. These advances enabled the arylation of a wide array of sterically encumbered amines, highlighting the importance of rational ligand design in facilitating challenging Pd-catalyzed cross-coupling reactions.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; cross-coupling; ligand design; palladium; synthetic methods

Mesh:

Substances:

Year:  2015        PMID: 26032920      PMCID: PMC4490068          DOI: 10.1002/anie.201502626

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  28 in total

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Journal:  Science       Date:  2003-10-31       Impact factor: 47.728

4.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

5.  Rapid and efficient microwave-assisted amination of electron-rich aryl halides without a transition-metal catalyst.

Authors:  Lei Shi; Min Wang; Chun-An Fan; Fu-Min Zhang; Yong-Qiang Tu
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

6.  Synthesis of alkylated aminofluorenes by palladium-catalyzed substitution at halofluorenes.

Authors:  Ginagunta Saroja; Zhang Pingzhu; Nikolaus P Ernsting; Jürgen Liebscher
Journal:  J Org Chem       Date:  2004-02-06       Impact factor: 4.354

7.  Umpolung amination: nickel-catalyzed coupling reactions of N,N-dialkyl-N-chloroamines with diorganozinc reagents.

Authors:  Timothy J Barker; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

8.  Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

Authors:  Michael G Organ; Mirvat Abdel-Hadi; Stephanie Avola; Igor Dubovyk; Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Mahmoud Sayah; Cory Valente
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues.

Authors:  Gerhard Bringmann; Tanja Gulder; Barbara Hertlein; Yasmin Hemberger; Frank Meyer
Journal:  J Am Chem Soc       Date:  2010-01-27       Impact factor: 15.419

10.  Discovery of ABT-267, a pan-genotypic inhibitor of HCV NS5A.

Authors:  David A DeGoey; John T Randolph; Dachun Liu; John Pratt; Charles Hutchins; Pamela Donner; A Chris Krueger; Mark Matulenko; Sachin Patel; Christopher E Motter; Lissa Nelson; Ryan Keddy; Michael Tufano; Daniel D Caspi; Preethi Krishnan; Neeta Mistry; Gennadiy Koev; Thomas J Reisch; Rubina Mondal; Tami Pilot-Matias; Yi Gao; David W A Beno; Clarence J Maring; Akhter Molla; Emily Dumas; Andrew Campbell; Laura Williams; Christine Collins; Rolf Wagner; Warren M Kati
Journal:  J Med Chem       Date:  2014-01-15       Impact factor: 7.446

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  14 in total

1.  Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

Authors:  Yike Zou; Xiangqin Li; Yun Yang; Simon Berritt; Jason Melvin; Stephen Gonzales; Matthew Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2018-07-20       Impact factor: 15.419

2.  Palladium-Catalyzed Arylation of Fluoroalkylamines.

Authors:  Andrew T Brusoe; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

3.  Well-defined nickel and palladium precatalysts for cross-coupling.

Authors:  Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal:  Nat Rev Chem       Date:  2017-03-01       Impact factor: 34.035

4.  Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling.

Authors:  Joseph M Dennis; Nicholas A White; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-03-22       Impact factor: 15.419

5.  Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands.

Authors:  Bryan T Ingoglia; Stephen L Buchwald
Journal:  Org Lett       Date:  2017-05-12       Impact factor: 6.005

Review 6.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

7.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

8.  Carbamate and N-Pyrimidine Mitigate Amide Hydrolysis: Structure-Based Drug Design of Tetrahydroquinoline IDO1 Inhibitors.

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Journal:  ACS Med Chem Lett       Date:  2021-02-26       Impact factor: 4.345

9.  Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis.

Authors:  Stanna K Dorn; Annika E Tharp; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-11       Impact factor: 16.823

10.  Biaryl Phosphine Based Pd(II) Amido Complexes: The Effect of Ligand Structure on Reductive Elimination.

Authors:  Pedro Luis Arrechea; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-09-13       Impact factor: 15.419

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