These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles.
    Author: Wang Z, Bachman S, Dudnik AS, Fu GC.
    Journal: Angew Chem Int Ed Engl; 2018 Oct 26; 57(44):14529-14532. PubMed ID: 30079625.
    Abstract:
    Nickel-catalyzed cross-coupling has emerged as the most versatile approach to date for achieving enantioconvergent carbon-carbon bond formation using racemic alkyl halides as electrophiles. In contrast, there have not yet been reports of the application of chiral nickel catalysts to the corresponding reactions with heteroatom nucleophiles to produce carbon-heteroatom bonds with good enantioselectivity. Herein, we establish that a chiral nickel/pybox catalyst can borylate racemic secondary benzylic chlorides to provide enantioenriched benzylic boronic esters, a highly useful family of compounds in organic synthesis. The method displays good functional group compatibility (e.g., being unimpeded by the presence of an indole, a ketone, a tertiary amine, or an unactivated alkyl bromide), and both of the catalyst components (NiCl2 ⋅glyme and the pybox ligand) are commercially available.
    [Abstract] [Full Text] [Related] [New Search]