Multicomponent-Multicatalyst Reactions (MC)2R: Efficient Dibenzazepine Synthesis
Jennifer Tsoung, Jane Panteleev, Matthias Tesch, and Mark Lautens
Org. Lett. 2014, 16, 110-113. DOI:10.1021/ol4030925 .
http://pubs.acs.org/doi/abs/10.1021/ol4030925
A RhI/Pd0 catalyst system was applied to the multicomponent synthesis of aza-dibenzazepines from vinylpyridines, arylboronic acids, and amines in a domino process with no intermediate isolation or purification.
5-(p-tolyl)-3-(trifluoromethyl)-10,11-dihydro-5H-benzo[b]pyrido[2,3-f]azepine (4a)
1H NMR
(400 MHz, CDCl3) δ 8.66 (d, J = 1.1 Hz, 1H), 7.97 (d, J = 1.8 Hz, 1H), 7.43 – 7.38 (m, 1H), 7.38 – 7.29
(m, 3H), 6.98 (d, J = 8.4 Hz, 2H), 6.57 – 6.51 (m, 2H), 3.33 – 3.21 (m, 2H), 3.09 – 2.99 (m, 2H), 2.26 (s,
3H);
13C NMR (101 MHz, CDCl3) δ 161.7 (q, J = 1.3 Hz), 145.8, 143.6, 143.4 (q, J = 4.0 Hz), 139.7,
139.5, 134.9 (q, J = 3.5 Hz), 130.3, 130.0, 129.9, 128.9, 128.2, 127.7, 125.3 (q, J = 33.1 Hz), 123.4 (q, J =
272.5 Hz), 114.0 (2), 35.9, 29.0, 20.4;
19F NMR (377 MHz, CDCl3) δ -62.0;
IR (NaCl, neat): 3063, 3028,
2926, 2862, 1616, 1506, 1489, 1456, 1435, 1429, 1410, 1339, 1319, 1296, 1267, 1240, 1207, 1165, 1128,
1086, 1036, 978, 947, 930, 910, 895, 808, 772, 756, 737, 721, 704, 687, 664, 646, 627 cm-1;
HRMS (ESI):
calcd for C21H18F3N2 (M+H)+: 355.1422; found. 355.1419.
Jennifer Tsoung
PhD graduate, organic chemistry
Experience
PhD
University of Toronto
– (5 years 2 months)
Research Intern
Kyoto University
– (3 months)Kyoto, Japan
Methodology project in asymmetric phase-transfer catalyzed alkylations.
Co-op student
Boehringer Ingelheim
– (8 months)Montreal, Canada Area
On two hit-to-lead teams working to synthesize analogues of hit compounds for HIV research.
Publications
Diastereoselective Friedel−Crafts Alkylation of Hydronaphthalenes(Link)
The Journal of Organic Chemistry
September 27, 2011
An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intramolecular Friedel-Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated…more
One-Pot Synthesis of Chiral Dihydrobenzofuran Framework via Rh/Pd Catlaysis
Organic Letters
October 12, 2012
A one-pot synthesis of the chiral dihydrobenzofuran framework is described. The method utilizes Rh-catalyzed asymmetric ring opening (ARO) and Pd-catalyzed C-O coupling to furnish the product in excellent enantioselectivity without isolation of intermediates. Systematic metal-ligand studies were carried out to investigate the compatibility of each catalytic system using product enantiopurity as an…more
Rh/Pd Catalysis with Chiral and Achiral Ligands: Domino Synthesis of Aza-Dihydrodibenzoxepines(Link)
Angew. Chem. Int. Ed
July 19, 2013
A game of dominoes: A synthetic route to aza-dihydrodibenzoxepines is described, through the combination of a Rh-catalyzed arylation and a Pd-catalyzed C-O coupling in a single pot. For the first time, the ability to incorporate a chiral and an achiral ligand in a two-component, two-metal transformation is achieved, giving the products in moderate to good yields, with excellent enantioselectivities.
Multicomponent-multicatalyst reactions (MC)(2)R: efficient dibenzazepine synthesis.
Organic Letters
January 13, 2014
A Rh(I)/Pd(0) catalyst system was applied to the multicomponent synthesis of aza-dibenzazepines from vinylpyridines, arylboronic acids, and amines in a domino process with no intermediate isolation or purification.
Formation of substituted oxa- and azarhodacyclobutanes.
Chemistry – A European Journal
December 6, 2013
The preparation of substituted oxa- and azarhodacyclobutanes is reported. After exchange of ethylene with a variety of unsymmetrically and symmetrically substituted alkenes, the corresponding rhodium-olefin complexes were oxidized with H2O2 and PhINTs (Ts=p-toluenesulfonyl) to yield the substituted oxa- and azarhodacyclobutanes, respectively. Oxarhodacyclobutanes could be prepared with excellent…more
Education
University of Toronto
Doctor of Philosophy (PhD), Organic Chemistry
Activities and Societies: Pueblo Science executive member, Let’s Talk Science volunteer, International Chemistry Olympiad tutor
The University of British Columbia
Bachelor of Science (BSc), Chemistry
Activities and Societies: Undergraduate Chemistry Society (UCS) executive member, Science Undergraduate Society (SUS) executive member, Science Co-op Students Association (SCOOPS) president and founding member
port moody secondary
High school
Mark Nitz presents Jennifer Tsoung certificate for her CTFP award
Women in Chemistry group, 2015
Lautens Research Group :: Group Pictures
University Professor
J. Bryan Jones Distinguished Professor
AstraZeneca Professor of Organic Chemistry
NSERC/Merck-Frosst Industrial Research Chair
Department of Chemistry
Davenport Chemical Laboratories
80 St. George St.
University of Toronto
Toronto, Ontario
M5S 3H6
Curriculum Vitae
Personal |
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| Place and Date of Birth | Hamilton, Ontario, Canada | July 9, 1959 |
Education |
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| Harvard University | NSERC PDF with D. A. Evans | 1985 – 1987 |
| University of Wisconsin-Madison | Ph.D. with B. M. Trost | 1985 |
| University of Guelph | B.Sc. – Distinction | 1981 |
Academic Positions |
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| J. Bryan Jones Distinguished Professor | University of Toronto | 2013 – 2018 |
| University Professor | University of Toronto | 2012 – present |
| NSERC/Merck Frosst Industrial Research Chair | NSERC/Merck Frosst | 2003 – 2013 |
| AstraZeneca Professor of Organic Synthesis | University of Toronto | 1998 – present |
| Professor | University of Toronto | 1995 – 1998 |
| Associate Professor | University of Toronto | 1992 – 1995 |
| Assistant Professor | University of Toronto | 1987 – 1992 |
Awards & Honors |
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| University of Toronto Alumni Faculty Award | University of Toronto | 2016 |
| CIC Catalysis Award | CSC | 2016 |
| Officer of the Order of Canada | Governor General | 2014 |
| Killam Research Fellowship | Canada Council for the Arts | 2013-2015 |
| CIC Medal | Chemical Institute of Canada | 2013 |
| Fellow of the Royal Society of UK | Royal Society of Chemistry | 2011 |
| Pedler Award | Royal Society of Chemistry | 2011 |
| Senior Scientist Award | Alexander von Humboldt Foundation Berlin, Aachen and Gottingen |
2009-2014 |
| Visiting Professor | University of Berlin | 2009 |
| Visiting Professor | Université de Marseilles | 2008 |
| ICIQ Summer School | ICIQ Tarragona, Spain | 2008 |
| Attilio Corbella Summer School Professor | Italian Chemical Society | 2007 |
| Arthur C. Cope Scholar Award | American Chemical Society | 2006 |
| Alfred Bader Award | Canadian Society for Chemistry | 2006 |
| R. U. Lemieux Award | Canadian Society for Chemistry | 2004 |
| Solvias Prize | Solvias AG | 2002 |
| Fellow of the Royal Society of Canada | Royal Society of Canada | 2001 |
Areas of Research Interest and Expertise |
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///////Multicomponent, Multicatalyst Reactions, (MC)2R, Dibenzazepine Synthesis, Mark Lautens, University of Toronto ,
Toronto, Ontario, Jennifer Tsoung
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