Versatile alkyl boronic reactivity : electrophilic fluorination and oxidative nucleophilic substitution for amide synthesis; O-Alkylation of phenols derivatives via a nucleophilic substitution

This thesis describes the study of the reactivity of boron compounds and the O-alkylation of aromatic alcohols. The use of boronic derivatives increased considerably over the past decades. There are used as cross-coupling partners in the Suzuki reaction and for 1,4 rhodium-catalyzed addition reaction. The nucleophilic nature of these compounds was induced by the C-B bond polarization. This peculiar reactivity was studied for the C-F bond formation. The use of Selectfluor® as fluorinating agent leads to good yields. Nevertheless, the polarity of the C-B bond could be reversed by oxidative nucleophilic substitution. Thus, C–N bond could be formed from nitriles and potassium trifluoroborate salts promoted by Cu(OAc)2 in the presence of BF3.OEt2. Due to the importance of ether chemistry in organic synthesis, the O-alkylation of phenol derivatives was achieved in the laboratory. From a stoichiometric amount of Lewis acid, BF3.OEt2, a catalytic system was developed involving cerium triflate. Then, the focus on green chemistry led to use a heterogeneous catalyst. Where Nafion® NR50 appears as a suitable catalyst for the ether synthesis

Data and Resources

Additional Info

Field Value
Source https://theses.hal.science/tel-00847776
Author Cazorla, Clément
Maintainer CCSD
Last Updated May 10, 2026, 05:57 (UTC)
Created May 10, 2026, 05:57 (UTC)
Identifier NNT: 2011LYO10144
Language fr
Rights https://about.hal.science/hal-authorisation-v1/
contributor Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS) ; Université Claude Bernard Lyon 1 (UCBL) ; Université de Lyon-Université de Lyon-École Supérieure de Chimie Physique Électronique de Lyon (CPE)-Institut National des Sciences Appliquées de Lyon (INSA Lyon) ; Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
creator Cazorla, Clément
date 2011-09-19T00:00:00
harvest_object_id 2043da1e-63e6-4177-92e4-28e320ace54d
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2026-03-31T00:00:00
set_spec type:THESE