A 4,4'-bipyridine-based catalyst system for diboration of pyrazine derivatives was established. The catalyst cycle consists of the following two steps: (1) reductive addition of the boron-boron bond of bis(pinacolato)diboron to 4,4'-bipyridine to form N,N'-diboryl-4,4'-bipyridinylidene and (2) oxidative boryl transfer from the intermediate to pyrazine to give N,N'-diboryl-1,4-dihydropyrazine with regeneration of 4,4'-bipyridine.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jacs.5b00546 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Total Syntheses of Nominal and Actual Prorocentin.
J Am Chem Soc
February 2023
Max-Planck-Institut für Kohlenforschung, 45478 Mülheim/Ruhr, Germany.
The dinoflagellate-derived polyether prorocentin is a co-metabolite of the archetypical serine/threonine phosphatase inhibitor okadaic acid. Whereas a structural relationship cannot be missed and a biosynthetic link was proposed, it is currently unknown whether there is any parallel in the bioactivity profile of these natural products. However, it was insinuated in the past that the structure assigned to prorocentin might need to be revised.
View Article and Find Full Text PDFAmine Catalysis for the Organocatalytic Diboration of Challenging Alkenes.
Chemistry
December 2016
Department of Chemistry, University of Hull, Cottingham Road, HU6 7RX, Hull, UK.
The generation of in situ sp -sp diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance.
View Article and Find Full Text PDFOrganocatalytic diboration involving "reductive addition" of a boron-boron σ-bond to 4,4'-bipyridine.
J Am Chem Soc
March 2015
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
A 4,4'-bipyridine-based catalyst system for diboration of pyrazine derivatives was established. The catalyst cycle consists of the following two steps: (1) reductive addition of the boron-boron bond of bis(pinacolato)diboron to 4,4'-bipyridine to form N,N'-diboryl-4,4'-bipyridinylidene and (2) oxidative boryl transfer from the intermediate to pyrazine to give N,N'-diboryl-1,4-dihydropyrazine with regeneration of 4,4'-bipyridine.
View Article and Find Full Text PDFAsymmetric organocatalytic diboration of alkenes.
Org Biomol Chem
September 2012
Dept. Química Física i Inorgànica, University Rovira i Virgili, Tarragona, Spain.
The use of chiral alcohols to form the Lewis acid-base *RO(-)→ bis(pinacolato)diboron adduct, in situ, provides an opportunity to induce asymmetry in the organocatalytic diboration of alkenes and complements the well established transition metal-mediated enantioselective diboration.
View Article and Find Full Text PDFCatalytic methodologies for the β-boration of conjugated electron deficient alkenes.
Org Biomol Chem
August 2012
Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK.
The area of boron conjugate addition via diboration (β-boration) has grown rapidly since the first examples appeared in the late 1990s. This article aims to give a comprehensive review of the current advances in β-boration (of electron deficient alkenes), providing a commentary upon the development of the asymmetric version. To date, many mechanistic models have been put forward to explain the experimental observations and this review surveys some of these key ideas.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!