Literature DB >> 28161943

Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron "Ate" Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger.

Gabriel J Lovinger1, Mark D Aparece1, James P Morken1.   

Abstract

Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables "ate" complex formation and overcomes catalytic inhibition by halide ions.

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Year:  2017        PMID： 28161943      PMCID： PMC5539536          DOI： 10.1021/jacs.6b12663

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


  25 in total

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2.  Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors:  Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal:  Science       Date:  2016-01-01       Impact factor: 47.728

3.  Mixed Mg/Li amides of the type R2NMgCl.LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds.

Authors:  Arkady Krasovskiy; Valeria Krasovskaya; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-28       Impact factor: 15.336

4.  Palladium-catalyzed carbon-carbon bond-forming 1,2-ligand migration of organoalanes.

Authors:  Eric Fillion; Rebekah J Carson; Vincent E Trépanier; Julie M Goll; Anna A Remorova
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

5.  Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate P,P ligand in Heck reactions.

Authors:  Christian Amatore; Béatrice Godin; Anny Jutand; Frédéric Lemaître
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

6.  Fine-tuning the nucleophilic reactivities of boron ate complexes derived from aryl and heteroaryl boronic esters.

Authors:  Guillaume Berionni; Artem I Leonov; Peter Mayer; Armin R Ofial; Herbert Mayr
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-21       Impact factor: 15.336

7.  Synthesis of amine-borane intramolecular complexes through palladium-catalyzed rearrangement of ammonioalkynyltriarylborates.

Authors:  Naoki Ishida; Mizuna Narumi; Masahiro Murakami
Journal:  Org Lett       Date:  2008-02-14       Impact factor: 6.005

8.  Reagent-controlled asymmetric homologation of boronic esters by enantioenriched main-group chiral carbenoids.

Authors:  Paul R Blakemore; Stephen P Marsden; Huw D Vater
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

9.  Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

Authors:  Marcin Odachowski; Amadeu Bonet; Stephanie Essafi; Philip Conti-Ramsden; Jeremy N Harvey; Daniele Leonori; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2016-07-22       Impact factor: 15.419

10.  Stereodivergent Olefination of Enantioenriched Boronic Esters.

Authors:  Roly J Armstrong; Cristina García-Ruiz; Eddie L Myers; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-13       Impact factor: 15.336
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  30 in total

1.  Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

Authors:  Yan Meng; Ziyin Kong; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

2.  Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Authors:  Chunyin Law; Yan Meng; Seung Moh Koo; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-04       Impact factor: 15.336

3.  Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.

Authors:  Jesse A Myhill; Liang Zhang; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-29       Impact factor: 15.336

4.  Enantioselective Synthesis of Nonracemic Geminal Silylboronates by Pt-Catalyzed Hydrosilylation.

Authors:  Adam A Szymaniak; Chenlong Zhang; John R Coombs; James P Morken
Journal:  ACS Catal       Date:  2018-02-23       Impact factor: 13.084

5.  Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

Authors:  Zhonglin Tao; Kevin A Robb; Jesse L Panger; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-11-09       Impact factor: 15.419

6.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

7.  Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

Authors:  Mark D Aparece; Chenpeng Gao; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-12       Impact factor: 15.336

8.  Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors:  Emma K Edelstein; Sheila Namirembe; James P Morken
Journal:  J Am Chem Soc       Date:  2017-03-29       Impact factor: 15.419

9.  Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Authors:  Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

10.  Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

Authors:  Matteo Chierchia; Chunyin Law; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336
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