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Tuesday, 7 June 2016

Multicomponent Multicatalyst Reactions (MC)2R: One-Pot Synthesis of 3,4-Dihydroquinolinones


Multicomponent Multicatalyst Reactions (MC)2R: 
One-Pot Synthesis of 3,4-Dihydroquinolinones
Lei Zhang, Lorenzo Sonaglia, Jason Stacey, and Mark Lautens Org. Lett. 2013152128-2131. DOI:10.1021/ol4006008 .

A Rh/Pd/Cu catalyst system led to an efficient synthesis of dihydroquinolinones in one-pot, two operations. The reaction features the first triple metal-catalyzed transformations in one reaction vessel, without any intermediate workup. The conjugate-addition/amidation/amidation reaction sequence is highly modular, divergent, and practical.


Multicomponent Multicatalyst Reactions (MC)2R: One-Pot Synthesis of 3,4-Dihydroquinolinones

Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada
Org. Lett.201315 (9), pp 2128–2131
DOI: 10.1021/ol4006008
Publication Date (Web): April 19, 2013
Copyright © 2013 American Chemical Society
http://pubs.acs.org/doi/abs/10.1021/ol4006008




Mark Lautens


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 BirthHamilton, Ontario, CanadaJuly 9, 1959

Education

Harvard UniversityNSERC PDF with D. A. Evans1985 - 1987
University of Wisconsin-MadisonPh.D. with B. M. Trost1985
University of GuelphB.Sc. - Distinction1981

Academic Positions

J. Bryan Jones Distinguished ProfessorUniversity of Toronto2013 - 2018
University ProfessorUniversity of Toronto2012 - present
NSERC/Merck Frosst Industrial Research ChairNSERC/Merck Frosst2003 - 2013
AstraZeneca Professor of Organic SynthesisUniversity of Toronto1998 - present
ProfessorUniversity of Toronto1995 - 1998
Associate ProfessorUniversity of Toronto1992 - 1995
Assistant ProfessorUniversity of Toronto1987 - 1992

Awards & Honors

University of Toronto Alumni Faculty AwardUniversity of Toronto2016
CIC Catalysis AwardCSC2016
Officer of the Order of CanadaGovernor General2014
Killam Research FellowshipCanada Council for the Arts2013-2015
CIC MedalChemical Institute of Canada2013
Fellow of the Royal Society of UKRoyal Society of Chemistry2011
Pedler AwardRoyal Society of Chemistry2011
Senior Scientist AwardAlexander von Humboldt Foundation
Berlin, Aachen and Gottingen
2009-2014
Visiting ProfessorUniversity of Berlin2009
Visiting ProfessorUniversité de Marseilles2008
ICIQ Summer SchoolICIQ Tarragona, Spain2008
Attilio Corbella Summer School ProfessorItalian Chemical Society2007
Arthur C. Cope Scholar AwardAmerican Chemical Society2006
Alfred Bader AwardCanadian Society for Chemistry2006
R. U. Lemieux AwardCanadian Society for Chemistry2004
Solvias PrizeSolvias AG2002
Fellow of the Royal Society of CanadaRoyal Society of Canada2001

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
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Saturday, 4 June 2016

Heterogeneous catalytic approaches in C-H activation reactions

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC00385K, Critical Review
Stefano Santoro, Sergei I. Kozhushkov, Lutz Ackermann, Luigi Vaccaro
This review summarizes the development of user-friendly, recyclable and easily separable heterogeneous catalysts for C-H activation during the last decade until December 2015.

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC00385K?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Despite the undisputed advances and progress in metal-catalyzed C–H functionalizations, this atom-economical approach had thus far largely been developed with the aid of various metal catalysts that were operative in a homogeneous fashion. 

While thereby major progress was accomplished, these catalytic systems featured notable disadvantages, such as low catalyst recyclability. This review summarizes the development of user-friendly, recyclable and easily separable heterogeneous catalysts for C–H activation.

This strategy was characterized by a remarkably broad substrate scope, considerable levels of chemo- and site-selectivities and proved applicable to C–C as well as C–heteroatom formation processes. 

Thus, recyclable catalysts were established for arylations, hydroarylations, alkenylations, acylations, nitrogenations, oxygenations, or halogenations, among others. The rapid recent progress in selective heterogeneous C–H functionalizations during the last decade until December 2015 is reviewed.


Heterogeneous catalytic approaches in C–H activation reactions

*
Corresponding authors
a
Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto, 8 – 06123 Perugia, Italy 
E-mail: luigi.vaccaro@unipg.it
Web: http://www.dcbb.unipg.it/greensoc
b
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany 
E-mail: Lutz.Ackermann@chemie.uni-goettingen.de
Web: http://www.ackermann.chemie.uni-goettingen.de
Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC00385K     




















Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto, 8 – 06123 Perugia, Italy 
E-mail: luigi.vaccaro@unipg.it
Web: http://www.dcbb.unipg.it/greensoc

Extra clips
 C-H Activation :: Wiley-VCH Hot Topics






 
 The Yu Lab
www.scripps.edu
"Ligand-Enabled Triple C-H Activation Reactions: One-Pot Synthesis of Diverse 4-Aryl-2-quinolinones from Propionamides" Angew. Chem. Int. Ed. 2014, 53, ...

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Saturday, 7 May 2016

N-Butylpyrrolidinone as a dipolar aprotic solvent for organic synthesis


Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC00932H, Paper
James Sherwood, Helen L. Parker, Kristof Moonen, Thomas J. Farmer, Andrew J. Hunt
N-Butylpyrrolidinone (NBP) has been demonstrated as a suitable safer replacement solvent for N-Methylpyrrolidinone (NMP) in selected organic syntheses.

N-Butylpyrrolidinone as a dipolar aprotic solvent for organic synthesis

*Corresponding authors
aGreen Chemistry Centre of Excellence, Department of Chemistry, University of York, UK
E-mail: andrew.hunt@york.ac.uk
bEastman Chemical Company, Pantserschipstraat 207 – B-9000, Gent, Belgium
Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC00932H
 
Dipolar aprotic solvents such as N-methylpyrrolidinone (or 1-methyl-2-pyrrolidone (NMP)) are under increasing pressure from environmental regulation. NMP is a known reproductive toxin and has been placed on the EU “Substances of Very High Concern” list. Accordingly there is an urgent need for non-toxic alternatives to the dipolar aprotic solvents. N-Butylpyrrolidinone, although structurally similar to NMP, is not mutagenic or reprotoxic, yet retains many of the characteristics of a dipolar aprotic solvent. This work introduces N-butylpyrrolidinone as a new solvent for cross-coupling reactions and other syntheses typically requiring a conventional dipolar aprotic solvent.

str1
////N-Butylpyrrolidinone, dipolar aprotic solvent , organic synthesis

Saturday, 30 April 2016

Dehydrogenative [2 + 2 + 1] Heteroannulation Using a Methyl Group as a One-Carbon Unit: Access to Pyrazolo[3,4-c]quinolines

 Figure

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
State Key Laboratory of Applied Organic Chemistry Lanzhou University, Lanzhou 730000, China
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.6b00618
Publication Date (Web): April 28, 2016
Copyright © 2016 American Chemical Society
*E-mail: srj0731@hnu.edu.cn., *E-mail: jhli@hnu.edu.cn.
 A practical and straightforward access to pyrazolo[3,4-c]quinolines by molecular sieve mediated dehydrogenative [2 + 2 + 1] heteroannulation of N-(o-alkenylaryl)imines with aryldiazonium salts is described using a sp3-hybrid carbon atom as a one-carbon unit. The reaction enables the formation of three new chemical bonds, a C–C bond and two C–N bonds, in a single reaction and features simple operation and excellent functional group tolerance.





/////////Dehydrogenative [2 + 2 + 1] Heteroannulation,   Pyrazolo[3,4-c]quinolines

Wednesday, 6 April 2016

Continuous-Flow Process for the Synthesis of m-Nitrothioanisole


Abstract Image
A continuous-flow process for the preparation of m-nitrothioanisole has been set up. The starting material m-nitroaniline was diazotized to give diazonium chloride, followed by azo-coupling with sodium thiomethoxide to give 1-(methylthio)-2-(3-nitrophenyl)diazene, then dediazoniated to gain m-nitrothioanisole in high yield. The continuous-flow process minimized accumulation of the energetic intermediate diazonium salt and has a better capacity for adapting large-scale production. A solvent was introduced in the azo-coupling section to create a biphasic flow system. Side products were inhibited eminently in this flow process.



Continuous-Flow Process for the Synthesis of m-Nitrothioanisole

Zhiqun Yu, Xiaoxuan Xie, Hei Dong, Jiming Liu, and Weike Su*
National Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. China
Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.6b00023
Publication Date (Web): March 24, 2016
Copyright © 2016 American Chemical Society
*Tel.: (+86)57188320899. E-mail: pharmlab@zjut.edu.cn.
http://pubs.acs.org/doi/abs/10.1021/acs.oprd.6b00023
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Monday, 21 March 2016

Eco-friendly construction of highly functionalized chromenopyridinones by an organocatalyzed solid-state melt reaction and their optical properties


Green Chem., 2016, 18,1488-1494
DOI: 10.1039/C5GC02658J, Paper
Sanjay Paul, Yong Rok Lee
Diverse chromenopyridinone derivatives were synthesized under organocatalytic solid-state melt conditions. The optical properties of these [small pi]-expanded chromenopyridine derivatives were examined.
The content of this RSS Feed (c) The Royal Society of Chemistry


http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C5GC02658J?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Eco-friendly construction of highly functionalized chromenopyridinones by an organocatalyzed solid-state melt reaction and their optical properties

Sanjay Paula and   Yong Rok Lee*a  
*
Corresponding authors
a
School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749, Republic of Korea
E-mail: yrlee@yu.ac.kr
Fax: +82-53-810-4631
Tel: +82-53-810-2529
Green Chem., 2016,18, 1488-1494

DOI: 10.1039/C5GC02658J


















The library construction of highly functionalized and diverse chromenopyridinones was achieved by three-component reactions of various 4-hydroxycoumarins with ammonium acetate and 3-formylchromones under L-proline catalyzed solid-state melt conditions. The advantages of this protocol include the use of an inexpensive organocatalyst, avoidance of toxic organic solvents, environmentally benign conditions, an easy work-up procedure and good to excellent product yields. The optical properties of these π-expanded varieties of the synthesized chromenopyridinone derivatives were also examined. A chromeno[4,3-b]pyridine nucleus bearing an electron donating group exhibited strong emission in the blue-green region of the visible spectrum.









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Saturday, 12 March 2016

High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention

Abstract Image.







High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention

The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering. California Institute of Technology, Pasadena, California 91125, United States
Materia, Inc., Pasadena, California 91107, United States
Org. Lett., 2016, 18 (4), pp 772–775
DOI: 10.1021/acs.orglett.6b00031
Publication Date (Web): February 03, 2016
Copyright © 2016 American Chemical Society

 http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b00031





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