个人简介

Dr. Barriault specializes in asymmetric synthesis, development of new synthetic methods and total synthesis of complex natural products. More precisely, he investigates the total synthesis of Garsubellin A, vinigrol, tetrodecamycin and related analogs, and of penostatin F.

研究领域

For many years, despite a rich coordination chemistry, gold was judged as being catalytically inactive for the formation of carbon-carbon bonds. In early 1970, few reports demonstrated that gold salts could be very useful reagents to catalyze organic transformations. Indeed, Au(I/III) complexes are soft Lewis acids which selectively coordinate to π-systems, notably, alkynes and allenes. As a result, this makes the substrate π-system deficient in electrons thus favoring the addition of nucleophiles. In the recent years, homogenous catalysis by gold has received considerable attention by the scientific community. The high affinity of Au(I/III) salt to alkyne and allene in the presence of many other functional groups and combined by its ability to stabilize cationic charge (e.g. gold carbene) provide tremendous opportunities for the discovery novel and useful reactions. Despite these advantages, applications of gold catalysis in stereoselective synthesis are still rare. Thrilled by the unique reactivity of gold complexes, our group tackle scientific problems of great interest by gold catalysis, domino reactions and their applications in total synthesis of complex natural products.

Our laboratory has always been interested in total synthesis and the challenge of building better and more ingenious ways to complex natural products.

近期论文

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Barriault, L.; McGee, P.; Bétournay, G.; Barabé, F. An 11-Step Total Synthesis of Magellanine through a Gold(I)-Catalyzed Dehydro Diels-Alder Reaction. Angew. Chem. Int. Ed. 2017, 56, in press. McCallum, T.; Rohe, S.; Barriault, L. Thieme Chemistry Journals Awardees – Where Are They Now? What’s Golden: Recent Advances in Organic Transformations Using Photoredox Gold Catalysis. Synlett. 2016, 27, A-Q (account) Barriault, L.; Tran, H.; McCallum, T.; Morin, M. Homocoupling of Iodoarenes and Bromoalkanes Using Photoredox Gold Catalysis: A Light Enabled Au(III) Reductive Elimination. Org Lett. 2016, 18, 4308. Barriault, L.; Cannillo, A.; Schwantje, T. R.; Bégin, M., Barabé, F. Gold-Catalyzed Photoredox C(sp2) Cyclization: Formal Synthesis of (±)-Triptolide. Org Lett. 2016, 18, 2592. Barriault, L.; McCallum, T. Direct Alkylation of Heteroarenes with Unactivated Bromoalkanes using Photoredox Gold Catalysis. Chem. Sci. 2016, 7, 4754. Barriault, L.; McCallum, T.; Jouanno, L.-A.; Cannillo, A. Persulfate-Enabled Direct C–H Alkylation of Heteroarenes with Unactivated Ethers. Synlett. 2016, 27, 1282. Barriault, L.; Scaiano, J. C.; McTiernan, C. D.; Morin, M.; McCallum, T. Polynuclear Gold(I) Complexes in Photoredox Catalysis: Understanding their Reactivity throught Characterization and Kinetic Analysis. Cat. Sci. Technol., 2016, 6, 201. Barriault, L.; Kaldas, S. J.; Cannillo, A.; McCallum, T. Indole Functionalization via Photoredox Gold Catalysis. Org Lett. 2015, 17, 2864. Barriault, L.; McGee, P.; Bellavance G.; Korobkov, I.; Tarasewicz, A. Synthesis and Isolation of Organogold Complexes via a Controlled 1,2-Silyl Migration. Chem. Eur. J. 2015, 21, 9662. Barriault, L.; McCallum, T. Light-Enabled Synthesis of Anhydrides and Amides, J. Org. Chem. 2015, 80, 2874. Barriault, L.; McCallum, T.; Morin, M.; Slavko, E. Light-Mediated Deoxygenation of Alcohols with a Dimeric Gold Catalyst. Eur. J. Org. Chem. 2015, 81. Barriault, L.; Bellavance, G. Total Syntheses of Hyperforin, Papuaforins A-C and Formal Synthesis of Nemorosone via a Gold(I)-Catalyzed Carbocyclization. Angew. Chem, Int. Ed. 2014, 53, 6701. Barriault, L.; Morin, M.; Levesque, P. Gold(I)-Catalyzed Domino Cyclizations for the Synthesis of Polyaromatic Heterocycles. Beils. J. Org. Chem. 2013, 9, 2625. Barriault, L.; Revol, G.; McCallum, T.; Morin, M.; Gagozs, Photoredox Transformations via Gold Dimeric Complexes. Angew Chem, Int. Ed. 2013, 52, 13342. Barriault, L.; Barabé, F.; Levesque, P.; Bellavance, G.; Sow, B., Gold-Catalyzed Synthesis of Bridged and Fused Carbocyles, Pure and Appl. Chem. 2013, 85, 1161. Barriault, L.; Denissova, I,; Goulet, N. Mechanistic Investigation of the Domino Oxy-Cope/Claisen/Ene Reaction and its Application to the Synthesis of Desdimethyl Ambiol B. Synthesis, 2012, 44, 1833. (invited contribution to a special issue on domino reaction, Ed. E. M. Carreira) Barriault, L.; Poulin, J, Grisé-Bard, C.M. Formal Synthesis of Vinigrol. Angew. Chem. Int., Ed 2012, 51, 2111. (VIP) Barriault, L. ; Barabé, F.; Levesque, P.; Korobkov. I. Synthesis of Fused Carbocycles via a Selective 6-endo dig Gold(I)-Catalyzed Carbocyclization. Org. Let. 2011, 13, 5580. Barriault, L. ; Sow, B.; Bellavance, G.; Barabé, F. Concise Synthesis of Bridgehead Ketone via Domino Gold-Catalyzed Cyclizations. Beils. J. Org. Chem. 2011, 7, 1007. (Invited contribution for a special issue in gold-catalyzed process)