Literature DB >> 34613744

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

Ryan P King1, Shane W Krska2, Stephen L Buchwald1.   

Abstract

The utilization of isolated Palladium Oxidative Addition Complexes (OACs) has had a significant impact on Pd-catalyzed and Pd-mediated cross-coupling reactions. Despite their importance, widespread utility of OACs has been limited by the instability of their precursor complexes. Herein, we report the use of Cámpora's palladacycle as a new, more stable precursor to Pd OACs. Using this palladacycle, a series of biarylphosphine ligated OACs, including those with pharmaceutical-derived aryl halides and relevance to bioconjugation, were prepared.

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Year:  2021        PMID: 34613744      PMCID: PMC9235910          DOI: 10.1021/acs.orglett.1c02307

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.072


  28 in total

1.  C─C Cleavage Approach to C─H Functionalization of Saturated Aza-Cycles.

Authors:  Jose B Roque; Yusuke Kuroda; Justin Jurczyk; Li-Ping Xu; Jin Su Ham; Lucas T Göttemann; Charis A Roberts; Donovon Adpressa; Josep Saurí; Leo A Joyce; Djamaladdin G Musaev; Charles S Yeung; Richmond Sarpong
Journal:  ACS Catal       Date:  2020-01-16       Impact factor: 13.084

2.  Pharmaceutical diversification via palladium oxidative addition complexes.

Authors:  Mycah R Uehling; Ryan P King; Shane W Krska; Tim Cernak; Stephen L Buchwald
Journal:  Science       Date:  2019-01-25       Impact factor: 47.728

3.  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

4.  Palladium-Protein Oxidative Addition Complexes by Amine-Selective Acylation.

Authors:  Heemal H Dhanjee; Ivan Buslov; Ian W Windsor; Ronald T Raines; Bradley L Pentelute; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419

5.  Synthesis and insertion reactions of the cyclometalated palladium-alkyl complexes Pd(CH(2)CMe(2)-o-C(6)H(4))L(2). Observation of a pentacoordinated intermediate in the insertion of SO(2).

Authors:  J Cámpora; J A López; P Palma; D del Rio; E Carmona; P Valerga; C Graiff; A Tiripicchio
Journal:  Inorg Chem       Date:  2001-08-13       Impact factor: 5.165

6.  Synthesis of benzocyclobutenes by palladium-catalyzed C-H activation of methyl groups: method and mechanistic study.

Authors:  Manon Chaumontet; Riccardo Piccardi; Nicolas Audic; Julien Hitce; Jean-Louis Peglion; Eric Clot; Olivier Baudoin
Journal:  J Am Chem Soc       Date:  2008-10-18       Impact factor: 15.419

7.  The History of Palladium-Catalyzed Cross-Couplings Should Inspire the Future of Catalyst-Transfer Polymerization.

Authors:  Amanda K Leone; Emily A Mueller; Anne J McNeil
Journal:  J Am Chem Soc       Date:  2018-11-01       Impact factor: 15.419

8.  Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.

Authors:  Scott D McCann; Elaine C Reichert; Pedro Luis Arrechea; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-08-24       Impact factor: 15.419

9.  Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods.

Authors:  Peter S Kutchukian; James F Dropinski; Kevin D Dykstra; Bing Li; Daniel A DiRocco; Eric C Streckfuss; Louis-Charles Campeau; Tim Cernak; Petr Vachal; Ian W Davies; Shane W Krska; Spencer D Dreher
Journal:  Chem Sci       Date:  2016-01-26       Impact factor: 9.825

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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  1 in total

1.  Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.

Authors:  James A R Tilden; Anneke T Lubben; Shaun B Reeksting; Gabriele Kociok-Köhn; Christopher G Frost
Journal:  Chemistry       Date:  2022-01-12       Impact factor: 5.020

  1 in total

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