Literature DB >> 21999801

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

Thomas J Maimone1, Phillip J Milner, Tom Kinzel, Yong Zhang, Michael K Takase, Stephen L Buchwald.   

Abstract

A mechanistic investigation of the Pd-catalyzed conversion of aryl triflates to fluorides is presented. Studies reveal that C-F reductive elimination from a LPd(II)(aryl)F complex (L = t-BuBrettPhos or RockPhos) does not occur when the aryl group is electron rich. Evidence is presented that a modified phosphine, generated in situ, serves as the actual supporting ligand during catalysis with such substrates. A preliminary study of the reactivity of a LPd(II)(aryl)F complex based on this modified ligand is reported.

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Year:  2011        PMID： 21999801      PMCID： PMC3354724          DOI： 10.1021/ja208461k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  29 in total

1.  Is fluoride bonded to two Pd acceptors still basic? Three CH2Cl2 molecules encapsulating a Pd2(mu-F)2 square and new implications for catalysis.

Authors:  Vladimir V Grushin; William J Marshall
Journal:  Angew Chem Int Ed Engl       Date:  2002-12-02       Impact factor: 15.336

2.  Palladium-mediated fluorination of arylboronic acids.

Authors:  Takeru Furuya; Hanns Martin Kaiser; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

Authors:  Kelvin S L Chan; Masayuki Wasa; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

4.  Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions.

Authors:  Simon Breitler; Nathan J Oldenhuis; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-05-23       Impact factor: 6.005

5.  Pd-catalyzed cross-coupling reactions of amides and aryl mesylates.

Authors:  Karin Dooleweerdt; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

6.  Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  Aryl-fluoride reductive elimination from Pd(II): feasibility assessment from theory and experiment.

Authors:  Dmitry V Yandulov; Ngon T Tran
Journal:  J Am Chem Soc       Date:  2007-02-07       Impact factor: 15.419

8.  An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides.

Authors:  Brett P Fors; Karin Dooleweerdt; Qingle Zeng; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

Review 9.  Carbon-fluorine bond formation.

Authors:  Takeru Furuya; Christian A Kuttruff; Tobias Ritter
Journal:  Curr Opin Drug Discov Devel       Date:  2008-11

10.  Synthesis and reactivity of a mono-sigma-aryl palladium(IV) fluoride complex.

Authors:  Nicholas D Ball; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419
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  31 in total

1.  Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Authors:  Ruth Dorel; Philip Boehm; Daniel P Schwinger; John F Hartwig
Journal:  Chemistry       Date:  2020-01-28       Impact factor: 5.236

2.  Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.

Authors:  Brad P Carrow; Jessica Sampson; Long Wang
Journal:  Isr J Chem       Date:  2019-12-13       Impact factor: 3.333

3.  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

4.  Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

5.  A bulky biaryl phosphine ligand allows for palladium-catalyzed amidation of five-membered heterocycles as electrophiles.

Authors:  Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-30       Impact factor: 15.336

6.  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

7.  Palladium(III)-catalyzed fluorination of arylboronic acid derivatives.

Authors:  Anthony R Mazzotti; Michael G Campbell; Pingping Tang; Jennifer M Murphy; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2013-09-16       Impact factor: 15.419

8.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

9.  Pd-catalyzed C-H fluorination with nucleophilic fluoride.

Authors:  Kate B McMurtrey; Joy M Racowski; Melanie S Sanford
Journal:  Org Lett       Date:  2012-07-30       Impact factor: 6.005

10.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419
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