Literature DB >> 25973673

Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters.

Kathryn Feeney1, Guillaume Berionni2, Herbert Mayr2, Varinder K Aggarwal1.   

Abstract

Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.

Entities:  

Year:  2015        PMID： 25973673     DOI： 10.1021/acs.orglett.5b00918

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


  11 in total

1.  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

2.  Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Authors:  Xinghua Ma; Mohamed Diane; Glenn Ralph; Christine Chen; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-04       Impact factor: 15.336

3.  Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Timothy J Barker
Journal:  Organometallics       Date:  2018-04-27       Impact factor: 3.876

4.  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.

Authors:  Gabriel J Lovinger; Mark D Aparece; James P Morken
Journal:  J Am Chem Soc       Date:  2017-02-16       Impact factor: 15.419

5.  Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

Authors:  Sophia G Gierszal; Timothy J Barker
Journal:  Tetrahedron Lett       Date:  2021-09-07       Impact factor: 2.032

6.  Benzylation of Imines with Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Jacob C Hayes; Timothy J Barker
Journal:  European J Org Chem       Date:  2019-01-21

7.  Nucleophilic Addition of Benzylboronates to Activated Ketones.

Authors:  Jacob C Hayes; Michael R Hollerbach; Timothy J Barker
Journal:  Tetrahedron Lett       Date:  2019-12-16       Impact factor: 2.415

8.  Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  Org Biomol Chem       Date:  2018-05-30       Impact factor: 3.876

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.  Alkynyl Moiety for Triggering 1,2-Metallate Shifts: Enantiospecific sp2 -sp3 Coupling of Boronic Esters with p-Arylacetylenes.

Authors:  Venkataraman Ganesh; Marcin Odachowski; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.