From arylboronic esters to arylnitrones : synthesis of arylboronic esters and new arylation reaction of cyclic nitrones.
type: Dataset
description: The first part is focused on the preparation of arylboronic esters derived from hexylene glycol, and bearing electron withdrawing substituents. We studied the palladium catalyzed borylation of electron-poor aryl halides with MPBH, an economic substitute for PinBH. MPBH, however, was found less efficient than PinBH. Next, a borylation through iodine/magnesium exchange with in situ trapping by the borate MPBOiPr was developed. This method allowed the borylation of aryl iodides carrying electron withdrawing and sensitive substituents, cleanly and safely (no accumulation of organomagnesium species), and scale up was possible (kilogram scale). Our attempts to use these arylboronic esters in addition reaction onto nitrones were unsuccessful. This led us to develop a new reaction: the direct arylation of cyclic nitrones with aryl halides. The coupling is dramatically accelerated by catalytic amounts of either a copper salt or pivalic acid. The reactions are fast and clean, and various (hetero)aryl iodides, bromides and chlorides can be used. Last, a mechanistic study allowed us to propose a mechanism for each additive.
identifier: NNT: 2012GRENV053
issued: 2026-05-11T06:00:26.872125
language: fr
modified: 2026-05-11T06:00:26.872129
contact point: Organization
  fn: CCSD
keyword: catalyse-organometallique
keyword: chimie-verte
keyword: infoeu-reposemanticsdoctoralthesis
keyword: methodologie-de-synthese
keyword: organometallic-catalysis
keyword: reactions-selective
keyword: sdvsalife-sciences-q-bioagricultural-sciences
keyword: selectivity
keyword: sustainable-chemistry
keyword: synthetic-methodology
keyword: theses
landing page: https://theses.hal.science/tel-00819878

From arylboronic esters to arylnitrones : synthesis of arylboronic esters and new arylation reaction of cyclic nitrones.
type: Distribution
format: HTML
issued: 2026-05-11T06:00:26.891015
modified: 2026-05-11T06:00:26.854287
access URL: https://theses.hal.science/tel-00819878

test_moissonnage_selune
type: Agent