2016-08-30



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

Jennifer Tsoung

PhD graduate, organic chemistry

Experience

PhD

University of Toronto

September 2010 – October 2015 (5 years 2 months)

Research Intern

Kyoto University

June 2014 – August 2014 (3 months)Kyoto, Japan

Methodology project in asymmetric phase-transfer catalyzed alkylations.

Co-op student

Angiotech

May 2009 – August 2009 (4 months)Vancouver, Canada Area

Formulation chemistry

Co-op student

Boehringer Ingelheim

January 2008 – August 2008 (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

2010 – 2014

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

2005 – 2010

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

www.chem.utoronto.ca

July 2013

Mark Lautens , O.C.

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

Tel: (416) 978-6083

Fax: (416) 946-8185

E-Mail: mlautens@chem.utoronto.ca

Curriculum Vitae

Personal

Place and Date of Birth

Hamilton, Ontario, Canada

July 9, 1959

Education

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

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

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

new synthetic methods

metal catalyzed cycloaddition and annulation reactions

asymmetric catalysis with focus on rhodium, nickel and palladium catalysts

cyclopropane synthesis and reactions

hydrometallation reactions

reactions of organosilicon and organotin compounds

fragmentation reactions

new routes to medicinally/biologically interesting compounds

heterocycle synthesis using metal catalysts

///////Multicomponent, Multicatalyst Reactions,  (MC)2R,  Dibenzazepine Synthesis, Mark Lautens, University of Toronto , Toronto, Ontario, Jennifer Tsoung

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