organic synthesis; asymmetric synthesis; radical reactions; organometallic reagents; organoboron chemistry; organocopper chemistry; alkaloids; natural products; chiral catalysts; non-toxic reagents; environmentally friendly processes
Gorokhovik Ioulia, Rieder Samuel, Povie Guillaume, Renaud Philippe (2014), Radical chain reactions involving 9-alkyl-9-borafluorenes, in
Arkivoc, 2014(3), 274-286.
Povie Guillaume, Tran Anh Tuan, Bonnaffé David, Habegger Jacqueline, Hu Zhaoyu, Le Narvor Christine, Renaud Philippe (2014), Repairing the thiol-ene coupling reaction, in
Angewandte Chemie - International Edition, 53(15), 3894-3898.
Dénès Fabrice, Pichowicz Mark, Povie Guillaume, Renaud Philippe (2014), Thiyl radicals in organic synthesis, in
Chemical Reviews, 114(5), 2587-2693.
Weidner Karin, Renaud Philippe (2013), Kinetic Study of the Radical Azidation with Sulfonyl Azides, in
AUSTRALIAN JOURNAL OF CHEMISTRY, 66(3), 341-345.
Weidner Karin, Renaud Philippe (2013), Kinetic Study of the Radical Azidation with Sulfonyl Azides, in
AUSTRALIAN JOURNAL OF CHEMISTRY, 66(3), 341-345.
Povie Guillaume, Renaud Philippe (2013), Lewis Acid-Water/Alcohol Complexes as Hydrogen Atom Donors in Radical Reactions, in
CHIMIA, 67(4), 250-252.
Povie Guillaume, Renaud Philippe (2013), Lewis Acid-Water/Alcohol Complexes as Hydrogen Atom Donors in Radical Reactions, in
CHIMIA, 67(4), 250-252.
Povie Guillaume, Marzorati Mattia, Bigler Peter, Renaud Philippe (2013), Role of Equilibrium Associations on the Hydrogen Atom Transfer from the Triethylborane-Methanol Complex, in
JOURNAL OF ORGANIC CHEMISTRY, 78(4), 1553-1558.
Brucelle Francois, Renaud Philippe (2013), Synthesis of a Leucomitosane via a Diastereoselective Radical Cascade, in
JOURNAL OF ORGANIC CHEMISTRY, 78(12), 6245-6252.
Denes Fabrice, Schiesser Carl H., Renaud Philippe (2013), Thiols, thioethers, and related compounds as sources of C-centred radicals, in
CHEMICAL SOCIETY REVIEWS, 42(19), 7900-7942.
Li Yi, Pouliot Martin, Vogler Thomas, Renaud Philippe, Studer Armido (2012), alpha-Aminoxylation of Ketones and beta-Chloro-alpha-aminoxylation of Enones with TEMPO and Chlorocatecholborane, in
ORGANIC LETTERS, 14(17), 4474-4477.
Renaud Philippe (2012), Boron in Radical Chemistry, in Chatgilialoglu Chryssostomos (ed.), Wiley, Chichester, 1-28.
Goncalves-Martin Monica G., Sigmantas Sarunas, Renaud Philippe (2012), Formal Synthesis of (-)-Cephalotaxine, in
HELVETICA CHIMICA ACTA, 95(12), 2502-2514.
Cao Lidong, Jimeno Ciril, Weidner Karin, Renaud Philippe (2012), Metal-Free, Radical Addition to Alkenes via Desulfitative Chlorine Atom Transfer (vol 18, pg 3467, 2011), in
ADVANCED SYNTHESIS & CATALYSIS, 354(11-12), 2070-2070.
Lapointe Guillaume, Kapat Ajoy, Weidner Karin, Renaud Philippe (2012), Radical azidation reactions and their application in the synthesis of alkaloids, in
PURE AND APPLIED CHEMISTRY, 84(7), 1633-1641.
Rouquet G, Robert F, Mereau R, Castet F, Renaud P, Landais Y (2012), Silylboranes as New Sources of Silyl Radicals for Chain-Transfer Reactions, in
CHEMISTRY-A EUROPEAN JOURNAL, 18(3), 940-950.
Brucelle Francois, Renaud Philippe (2012), Synthesis of Indolines, Indoles, and Benzopyrrolizidinones from Simple Aryl Azides, in
ORGANIC LETTERS, 14(12), 3048-3051.
Brucelle F, Renaud P (2012), Synthesis of Indolines, Indoles, and Benzopyrrolizidinones from Simple Aryl Azides, in
ORGANIC LETTERS, 14(12), 3048-3051.
Maury Julien, Feraya Laurence, Bertrand Michele P., Kapat Ajoy, Renaud Philippe (2012), Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines, in
TETRAHEDRON, 68(47), 9606-9611.
Kapat A, Konig A, Montermini F, Renaud P (2011), A Radical Procedure for the Anti-Markovnikov Hydroazidation of Alkenes, in
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 133(35), 13890-13893.
Lapointe G, Schenk K, Renaud P (2011), Concise Synthesis of Pyrrolidine and Indolizidine Alkaloids by a Highly Convergent Three-Component Reaction, in
CHEMISTRY-A EUROPEAN JOURNAL, 17(11), 3207-3212.
Abazi S, Rapado LP, Renaud P (2011), Diastereoselective radical mediated alkylation of a chiral glycolic acid derivative, in
ORGANIC & BIOMOLECULAR CHEMISTRY, 9(16), 5773-5777.
Cao LD, Weidner K, Renaud P (2011), Metal-Free, Radical Addition to Alkenes via Desulfitative Chlorine Atom Transfer, in
ADVANCED SYNTHESIS & CATALYSIS, 353(18), 3467-3472.
Luthy M, Darmency V, Renaud P (2011), Modified B-Alkylcatecholboranes as Radical Precursors, in
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (3), 547-552.
Lamarque C, Beaufils F, Denes F, Schenk K, Renaud P (2011), Preparation of 5-Membered Rings via Radical Addition-Translocation-Cyclization (RATC) Processes Mediated by Diethyl Thiophosphites, in
ADVANCED SYNTHESIS & CATALYSIS, 353(8), 1353-1358.
Villa G, Povie G, Renaud P (2011), Radical Chain Reduction of Alkylboron Compounds with Catechols, in
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 133(15), 5913-5920.
Lapointe G, Schenk K, Renaud P (2011), Total Synthesis of (+/-)-Cylindricine C, in
ORGANIC LETTERS, 13(18), 4774-4777.
The total synthesis of natural products and analogues proved over the years to be a very reliable method for the discovery of new drugs. Due the structural complexity of many natural products, efficient synthetic methods are required to synthesize them in order to make them (as well as analogues) available to scientists involved in drug discovery. Our research program aims at finding methods and strategies that can be applied for efficient synthesis of different classes of products possessing an interesting biological profile. Development of processes involving radical chemistry, organometallic chemistry and enantioselective catalysis will be investigated. Our research focus on increasing the efficiency of target molecule synthesis by minimizing the number of synthetic steps, by opening new synthetic pathways, and by developing environmentally friendly reagents. The project is subdivided in three sub-chapters according to synthetic methods:Boron reagents for radical chemistry. Radical reactions have been intensively investigated during the last two decades. The new synthetic methods that aroused from this work are characterized by their mildness and their complement to ionic processes. The potential of these reactions is immense as demonstrated by their recent use in the synthesis of complex natural products. Our effort will be concentrated on the development of non-toxic and environmentally friendly reagents to perform efficient radical reactions. Organoboranes will be used to generate radicals that are functionalized close to the radical center. The extremely rich chemistry of organoboron species will play a crucial role in developing these new reagents. The combination of organoborane chemistry with the chemistry of well-established antioxidants will also be investigated in order to develop a simple an efficient procedure to reduce radicals and to run unique radical rearrangements.Azide chemistry. The formation of carbon-nitrogen bonds under very mild reaction conditions represents a very useful tool for the total synthesis of alkaloids. Reagents and procedures to prepare alkyl azides via radical pathways are explored. They will allow the development of highly efficient and practical syntheses of polycyclic alkaloids isolated from marine organisms (cylindricines) and plants (aspidosperma alkaloids). A unique rearrangement of alkyl azides, the intramolecular Schmidt reaction, has been for the first time run under non-acidic conditions. Further development of this process is expected to offer exceptional opportunities for the preparation of complex alkaloid skeletons in an excitingly concise manner.Organocopper chemistry. Due to their exceptional reactivity, organocopper reagents play a unique role in organic synthesis. Two reactions will be investigated. The first process is an original annulation procedure that affords fused bicyclic systems in one step via a cascade reaction. The second process concerns the generation of congested quaternary amino substituted carbon centers. In a one-pot process, up to three carbon-carbon bond will be created. Applications for the synthesis of polycyclic Cephalotaxus and Erythrina alkaloids are foreseen.