Literature DB >> 31896889

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

Bryan T Ingoglia1, Corin C Wagen1, Stephen L Buchwald1.   

Abstract

Over the past three decades, Pd-catalyzed cross-coupling reactions have become a mainstay of organic synthesis. In particular, catalysts derived from biaryl monophosphines have shown wide utility in forming C-N bonds under mild reaction conditions. This work summarizes a variety of C-N cross-coupling reactions using biaryl monophosphines as supporting ligands, with the goal of directing synthetic chemists towards the ligands and conditions best suited for a particular coupling.

Entities:  

Year:  2019        PMID： 31896889      PMCID： PMC6939672          DOI： 10.1016/j.tet.2019.05.003

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


  61 in total

1.  Generating Active "L-Pd(0)" via Neutral or Cationic π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions.

Authors:  A J DeAngelis; Peter G Gildner; Ruishan Chow; Thomas J Colacot
Journal:  J Org Chem       Date:  2015-06-15       Impact factor: 4.354

2.  Palladium-catalyzed N-arylation of 2-aminothiazoles.

Authors:  Meredeth A McGowan; Jaclyn L Henderson; Stephen L Buchwald
Journal:  Org Lett       Date:  2012-03-06       Impact factor: 6.005

3.  Efficient Pd-catalyzed amination reactions for heterocycle functionalization.

Authors:  Jaclyn L Henderson; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

4.  Monoligated palladium species as catalysts in cross-coupling reactions.

Authors:  Ute Christmann; Ramón Vilar
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

5.  Synthesis and pharmacological investigation of new N-hydroxyalkyl-2-aminophenothiazines exhibiting marked MDR inhibitory effect.

Authors:  Daniella Takács; Orsolya Egyed; László Drahos; Pál Szabó; Katalin Jemnitz; Mónika Szabó; Zsuzsa Veres; Júlia Visy; József Molnár; Zsuzsanna Riedl; György Hajós
Journal:  Bioorg Med Chem       Date:  2013-04-23       Impact factor: 3.641

6.  An efficient process for pd-catalyzed C-N cross-coupling reactions of aryl iodides: insight into controlling factors.

Authors:  Brett P Fors; Nicole R Davis; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

7.  Cascade palladium catalysis: a predictable and selectable regiocontrolled synthesis of N-arylbenzimidazoles.

Authors:  Nathan T Jui; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-13       Impact factor: 15.336

8.  Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions.

Authors:  Nicolas Marion; Steven P Nolan
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

9.  Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

Authors:  Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-12-14       Impact factor: 15.419

10.  N-substituted 2-aminobiphenylpalladium methanesulfonate precatalysts and their use in C-C and C-N cross-couplings.

Authors:  Nicholas C Bruno; Nootaree Niljianskul; Stephen L Buchwald
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
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  19 in total

1.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

2.  Improved Process for the Palladium-Catalyzed C-O Cross-Coupling of Secondary Alcohols.

Authors:  Hong Zhang; Paula Ruiz-Castillo; Alexander W Schuppe; Stephen L Buchwald
Journal:  Org Lett       Date:  2020-06-24       Impact factor: 6.005

3.  Cooperative Pd/Cu Catalysis for Alkene Arylboration: Opportunities for Divergent Reactivity.

Authors:  Stanna K Dorn; M Kevin Brown
Journal:  ACS Catal       Date:  2022-01-24       Impact factor: 13.700

4.  [(NHC)PdCl2(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions.

Authors:  Qinqin Xia; Shicheng Shi; Pengcheng Gao; Roger Lalancette; Roman Szostak; Michal Szostak
Journal:  J Org Chem       Date:  2021-10-07       Impact factor: 4.198

5.  Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.

Authors:  Sii Hong Lau; Peng Yu; Liye Chen; Christina B Madsen-Duggan; Michael J Williams; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2020-11-12       Impact factor: 15.419

6.  Aerobic Catalyzed Oxidative Cross-Coupling of N,N-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.

Authors:  Thomas J Paniak; Marisa C Kozlowski
Journal:  Org Lett       Date:  2020-02-12       Impact factor: 6.005

7.  A Ligand Exchange Process for the Diversification of Palladium Oxidative Addition Complexes.

Authors:  Ryan P King; Shane W Krska; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-07-28       Impact factor: 6.072

8.  Amphiphilic Biaryl Monophosphine Ligands by Regioselective Sulfonation.

Authors:  Jacob Rodriguez; Heemal H Dhanjee; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-01-21       Impact factor: 6.005

9.  Pd-Catalyzed Alkene Diamination Reactions with O-Benzoylhydroxylamine Electrophiles: Evidence Supporting a Pd(II/IV) Catalytic Cycle, the Role of 2,4-Pentanedione Derivatives as Ligands, and Expanded Substrate Scope.

Authors:  Janelle K Kirsch; Gabriel A Gonzalez; Mason S Faculak; John P Wolfe
Journal:  J Org Chem       Date:  2021-08-04       Impact factor: 4.198

10.  C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)2 or CuI.

Authors:  Yoshihide Usami; Yuya Tatsui; Hiroki Yoneyama; Shinya Harusawa
Journal:  Molecules       Date:  2020-10-12       Impact factor: 4.411
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