Literature DB >> 28498667

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

Bryan T Ingoglia1, Stephen L Buchwald1.   

Abstract

In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The precatalysts described herein are easily prepared and stable to long-term storage under air.

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Year:  2017        PMID: 28498667      PMCID: PMC5580394          DOI: 10.1021/acs.orglett.7b01082

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  23 in total

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

Authors:  Nathaniel H Park; Ekaterina V Vinogradova; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

2.  Structure and Reactivity of [(L•Pd)n•(1,5-cyclooctadiene)] (n=1-2) Complexes Bearing Biaryl Phosphine Ligands.

Authors:  Hong Geun Lee; Phillip J Milner; Michael T Colvin; Loren Andreas; Stephen L Buchwald
Journal:  Inorganica Chim Acta       Date:  2014-10-01       Impact factor: 2.545

Review 3.  C-N bond forming cross-coupling reactions: an overview.

Authors:  Jitender Bariwal; Erik Van der Eycken
Journal:  Chem Soc Rev       Date:  2013-09-30       Impact factor: 54.564

4.  Dual effect of halides in the Stille reaction: in situ halide metathesis and catalyst stabilization.

Authors:  Stefan Verbeeck; Caroline Meyers; Philippe Franck; Anny Jutand; Bert U W Maes
Journal:  Chemistry       Date:  2010-11-15       Impact factor: 5.236

5.  Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.

Authors:  Donald A Watson; Mingjuan Su; Georgiy Teverovskiy; Yong Zhang; Jorge García-Fortanet; Tom Kinzel; Stephen L Buchwald
Journal:  Science       Date:  2009-08-13       Impact factor: 47.728

6.  Palladium-catalyzed hydroxylation of aryl and heteroaryl halides enabled by the use of a palladacycle precatalyst.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2014-05-06       Impact factor: 4.354

7.  Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates.

Authors:  Sandra M King; Stephen L Buchwald
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005

8.  Dosage delivery of sensitive reagents enables glove-box-free synthesis.

Authors:  Aaron C Sather; Hong Geun Lee; James R Colombe; Anni Zhang; Stephen L Buchwald
Journal:  Nature       Date:  2015-08-13       Impact factor: 49.962

9.  The Evolution of Pd0/PdII-Catalyzed Aromatic Fluorination.

Authors:  Aaron C Sather; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2016-09-22       Impact factor: 22.384

10.  A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.

Authors:  Aaron C Sather; Hong Geun Lee; Valentina Y De La Rosa; Yang Yang; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-10-06       Impact factor: 15.419

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  7 in total

1.  Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases.

Authors:  Jessica Xu; Richard Y Liu; Charles S Yeung; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-06-21       Impact factor: 13.084

2.  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

3.  Unexpected Formation of Hexasubstituted Arenes through a 2-fold Palladium-Mediated Ligand Arylation.

Authors:  Corin C Wagen; Bryan T Ingoglia; Stephen L Buchwald
Journal:  J Org Chem       Date:  2019-09-25       Impact factor: 4.354

4.  A Neophyl Palladacycle as an Air- and Thermally Stable Precursor to Oxidative Addition Complexes.

Authors:  Ryan P King; Shane W Krska; Stephen L Buchwald
Journal:  Org Lett       Date:  2021-10-06       Impact factor: 6.072

5.  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

6.  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

7.  An Improved PIII/PV═O-Catalyzed Reductive C-N Coupling of Nitroaromatics and Boronic Acids by Mechanistic Differentiation of Rate- and Product-Determining Steps.

Authors:  Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-03-25       Impact factor: 15.419

  7 in total

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