Multicomponent Multicatalyst Reactions (MC)2R:  One-Pot Synthesis of 3,4-Dihydroquinolinones Lei Zhang, Lorenzo Sonaglia, Jason Stacey, and Mark Lautens Org. Lett. 2013, 15, 2128-2131. 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 Lei Zhang, Lorenzo Sonaglia, Jason Stacey, and Mark Lautens* Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St George Street, Toronto, Ontario M5S 3H6, Canada Org. Lett., 2013, 15 (9), pp 2128–2131 DOI: 10.1021/ol4006008 Publication Date (Web): April 19, 2013 Copyright © 2013 American Chemical Society mlautens@chem.utoronto.ca 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 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 ////////////

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

Stefano Santoro,^a   Sergei I. Kozhushkov,^b  Lutz Ackermann*^b and   Luigi Vaccaro*^a  

*

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

www.wiley-vch.de

 
 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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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

N-Butylpyrrolidinone as a dipolar aprotic solvent for organic synthesis

James Sherwood,^a   Helen L. Parker,^a   Kristof Moonen,^b  Thomas J. Farmer^a and   Andrew J. Hunt*^a  

*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

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC00932H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

 

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.

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

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

 

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

Guo-Bo Deng^†, Hai-Bing Li^†, Xu-Heng Yang^†, Ren-Jie Song^*†, Ming Hu^†, and Jin-Heng Li^*†‡

^† 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.

http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b00618

 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

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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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

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

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 Paul^a and   Yong Rok Lee*^a  

Hide Affiliations

*

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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.

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

Adam M. Johns^†, Tonia S. Ahmed^‡, Bradford W. Jackson^†, Robert H. Grubbs^*‡, and Richard L. Pederson^*†

^‡ 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

*E-mail: rhg@caltech.edu., *E-mail: rpederson@materia-inc.com.

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





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