The Synthesis of Biarylmonophosphonates via Palladium-Catalyzed Phosphonation, Iridium-Catalyzed C-H Borylation, Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling

The iridium-catalyzed C-H borylation of diethyl phenylphosphonate results in nonselective mono and bisborylation to afford a near statistical mixture of 3-, 3,5- and 4-boryl substituted aryl phosphonates whereas 3-substituted aryl phosphonates undergo highly regioselective C-H borylation to afford t...

Full description

Saved in:
Bibliographic Details
Published in:Catalysis letters 2022-02, Vol.152 (2), p.398-413
Main Authors: Doherty, Simon, Knight, Julian G., Tran, Tina S. T., Alharbi, Hussam Y., Perry, Daniel O.
Format: Article
Language:English
Subjects:
Aromatic compounds
Catalysis
Chemical synthesis
Chemical tests and reagents
Chemistry
Chemistry and Materials Science
Cross coupling
Esters
Industrial Chemistry/Chemical Engineering
Iridium
Organometallic Chemistry
Palladium
Phenyl phosphonate
Phosphonates
Physical Chemistry
Reagents
Substitutes
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The iridium-catalyzed C-H borylation of diethyl phenylphosphonate results in nonselective mono and bisborylation to afford a near statistical mixture of 3-, 3,5- and 4-boryl substituted aryl phosphonates whereas 3-substituted aryl phosphonates undergo highly regioselective C-H borylation to afford the corresponding meta -phosphonate substituted arylboronic esters as the sole product; the resulting boronic esters were used as nucleophilic reagents in a subsequent palladium-catalyzed Suzuki–Miyaura cross-coupling to generate a range of biarylmonophosphonates. Gratifyingly, the Suzuki–Miyaura cross-coupling can be conducted without purifying the boronic ester which greatly simplifies the synthetic procedure. Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-021-03643-3