Literature DB >> 25346547

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

Hong Geun Lee1, Phillip J Milner1, Michael T Colvin1, Loren Andreas1, Stephen L Buchwald1.   

Abstract

The structure of the stable Pd(0) precatalyst [(1,5-cyclooctadiene)(L•Pd)2] (L = AdBrettPhos) for the Pd-catalyzed fluorination of aryl triflates has been further studied by solid state NMR and X-ray cystrallography of the analogous N-phenylmaleimide complex. The reactivity of this complex with CDCl3 to form a dearomatized complex is also presented. In addition, studies suggest that related bulky biaryl phosphine ligands form similar complexes, although the smaller ligand BrettPhos forms a monomeric [(1,5-cyclooctadiene)(L•Pd)] species instead.

Entities:  

Keywords:  Pd(0) complex; biaryl phosphine; oxidative addition; precatalyst

Year:  2014        PMID: 25346547      PMCID: PMC4206912          DOI: 10.1016/j.ica.2014.06.008

Source DB:  PubMed          Journal:  Inorganica Chim Acta        ISSN: 0020-1693            Impact factor:   2.545


  13 in total

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Authors:  Jesse R McAtee; Sara E S Martin; Derek T Ahneman; Keywan A Johnson; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-01       Impact factor: 15.336

4.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

5.  The palladium-catalyzed trifluoromethylation of aryl chlorides.

Authors:  Eun Jin Cho; Todd D Senecal; Tom Kinzel; Yong Zhang; Donald A Watson; Stephen L Buchwald
Journal:  Science       Date:  2010-06-25       Impact factor: 47.728

6.  Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides.

Authors:  Thomas J Maimone; Phillip J Milner; Tom Kinzel; Yong Zhang; Michael K Takase; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

7.  An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors:  Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Adv Synth Catal       Date:  2012-06-27       Impact factor: 5.837

8.  Synthesis and application of palladium precatalysts that accommodate extremely bulky di-tert-butylphosphino biaryl ligands.

Authors:  Nicholas C Bruno; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-05-15       Impact factor: 6.005

9.  An improved catalyst system for the Pd-catalyzed fluorination of (hetero)aryl triflates.

Authors:  Hong Geun Lee; Phillip J Milner; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005

10.  Pd-catalyzed nucleophilic fluorination of aryl bromides.

Authors:  Hong Geun Lee; Phillip J Milner; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-02-27       Impact factor: 15.419

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  15 in total

1.  Virtually instantaneous, room-temperature [(11)C]-cyanation using biaryl phosphine Pd(0) complexes.

Authors:  Hong Geun Lee; Phillip J Milner; Michael S Placzek; Stephen L Buchwald; Jacob M Hooker
Journal:  J Am Chem Soc       Date:  2015-01-09       Impact factor: 15.419

2.  Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.

Authors:  Jesse R McAtee; Sarah B Krause; Donald A Watson
Journal:  Adv Synth Catal       Date:  2015-07-14       Impact factor: 5.837

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Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

4.  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

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

6.  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

7.  Palladium-Mediated Arylation of Lysine in Unprotected Peptides.

Authors:  Hong Geun Lee; Guillaume Lautrette; Bradley L Pentelute; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-16       Impact factor: 15.336

8.  A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions.

Authors:  Sarah B Krause; Jesse R McAtee; Glenn P A Yap; Donald A Watson
Journal:  Org Lett       Date:  2017-09-29       Impact factor: 6.005

9.  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

10.  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

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