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Sunday, 25 September 2016

A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives

Image result for A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives








A highly efficient and green method has been developed for the rapid preparation of highly functionalized isoxazolopyridin-3-amine derivatives in excellent yields. This process has a broad substrate scope, is operationally simple, and generally requires no chromatographic purification. In addition, the process is scalable and significantly greener than current alternatives with a PMI of 18 and water as the reaction solvent.



Graphical abstract: A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives


Image result for A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives

Image result for A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives









































Image result for A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives











Image result for A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives


Image result for A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives



A rapid preparation of highly functionalized isoxazolopyridin-3-amine and other heterocyclic fused aminoisoxazole derivatives


A high-yielding method for the preparation of isoxazolopyridin-3-amine derivatives

Wensheng Yu,*a   Paul G. Bulgerb and   Kevin M. Maloney*b  

*
Corresponding authors
a
Discovery Chemistry, Merck Research Laboratories, 126 E. Lincoln Avenue, Rahway, USA
E-mail: wensheng.yu@merck.com
b
Process Chemistry, Merck Research Laboratories, 126 E. Lincoln Avenue, Rahway, USA
Green Chem., 2016,18, 4941-4946

DOI: 10.1039/C6GC01125J















http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC01125J?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract


Wensheng Yu


Wensheng Yu

Associate Principal Scientist at Merck



Image result for Paul G. Bulger merck

Paul G. Bulger was born in London, England, in 1978. He received his undergraduate M.Chem degree in 2000 from the University of Oxford, completing his Part II project under the supervision of Dr. Mark G. Moloney. He remained at Oxford for his graduate studies, obtaining his D. Phil. in chemistry in 2003 for research conducted under the supervision of Professor Sir Jack E. Baldwin. After an enjoyable three-year stint as a postdoctoral researcher in Professor K. C. Nicolaou's group at The Scripps Research Institute, he joined the Process Research Department of Merck & Co., Inc. in the fall of 2006.






pic not available



Kevin Maloney

Sr Research Chemist at Merck Sharp & Dohme


Experience


Sr Research Chemist

Merck
 – Present (9 years)

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Friday, 23 September 2016

A Simple and Versatile Reactor for Photochemistry

Abstract Image
A photoreactor that generates a thin film upon rotation for efficient irradiation of solutions is described. The reactor is based around a standard piece of equipment found in most synthetic laboratories, namely, a rotary evaporator. Three different photo-oxidation reactions have been used to examine the effects of several parameters such as irradiated volume, flask size, rotation speed, and light intensity. The reactor can be operated in a semicontinuous manner, and two possible configurations are described. The thickness of the generated film and the rate of mixing under different conditions have been examined using in situ electronic absorption spectroscopy.

Safety warning: Any experiment involving flammable organic solvents and air or pure oxygen is potentially hazardous, especially when partially contained, as is the case of the flask of our reactor. We took the following precautions and encountered no problems but we stress the need for readers to make safety assessments for their own experiments as peripheral circumstances may be different from ours. All experiments were carried out in a fume hood or ventilated enclosure with adequate ventilation and the front lowered. Any obvious sources of ignition were removed. Oxygen was fed from a cylinder fitted with a compliant regulator and was delivered at a maintained pressure of 1 bar using a mass flow controller compatible with oxygen. The equipment was maintained and cleaned free of grease at all times to prevent any incompatibilities with oxygen. Temperatures were kept at ambient. When working above the solvent flash point and LOC, care must be taken to ensure that all possible risks have been considered. Appropriate safeguards and suitable safety measures must be implemented.




A Simple and Versatile Reactor for Photochemistry

School of Chemistry, Department of Mechanical, Materials and Manufacturing Engineering, The University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom
§ Department of Chemical and Environmental Engineering, The University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, China
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.6b00257
*E-mail: martyn.poliakoff@nottingham.ac.uk (M.P.)., *E-mail: mike.george@nottingham.ac.uk (M.W.G.).

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Monday, 19 September 2016

Solid-Phase Peptide Synthesis of Dipeptide (Histidine-β-Alanine) as a Chelating Agent by Using Trityl Chloride Resin, for Removal of Al3+, Cu2+, Hg2+ and Pb2+: Experimental and Theoretical Study




Characterization of synthesised dipeptide (histidine-β- alanine) Dipeptide was successfully synthesized via the standard BOC method. The synthesis of dipeptide (histidine-β- alanine) was approved by using UV-Vis, FTIR, 1 H NMR and LC-MS analysis. The UV-Vis absorbance spectra of histidine-β-alanine obtained in water at 25 °C is presented in Figure 1. The results show that the maximum peaks were appeared at 214 and 264 nm, which can be assigned to π→π* and n→π*, respectively.
FTIR (KBr) n / cm−1 3226 (NH2), 1641 (amide), 1563 (imidazol);

1H NMR (300 MHz, D2O) d 2.60 (m, 2 Hs, 12H), 2.92 (dd, 1 Hs, 6H), 3.08 (dd, 1 Hs, 6H), 3.16 (m, 2 Hs, 11H), 4.40 (dd, 1 Hs, 7H), 6.89 (s, 1 Hs, 4H), 7.66 (dd, 1 Hs, 2H), 7.89 (imidazole ring).

The LC-MS analysis showed a single mass peak in [M + H]+ and [M]− , which
correspond to molecular weight for dipeptide calculated for C9H14N4O3: 226.23; found m/z [M + H]+ : 227.000 and m/z [M]− : 224.800 (Figure 2).












J. Braz. Chem. Soc. 2016, 27(10), 1814-1819

Solid-Phase Peptide Synthesis of Dipeptide (Histidine-β-Alanine) as a Chelating Agent by Using Trityl Chloride Resin, for Removal of Al3+, Cu2+, Hg2+ and Pb2+: Experimental and Theoretical Study


Rahmatollah Rahimi; Maryam Khosravi; Mohammd H. H. Tehrani; Mahboubeh Rabbani; Ebrahim Safavi





Rahimi R, Khosravi M, Tehrani MHH, Rabbani M, Safavi E. Solid-Phase Peptide Synthesis of Dipeptide (Histidine-β-Alanine) as a Chelating Agent by Using Trityl Chloride Resin, for Removal of Al3+, Cu2+, Hg2+ and Pb2+: Experimental and Theoretical Study. J. Braz. Chem. Soc. 2016;27(10):1814-1819



Solid-phase peptide synthesis of dipeptide (histidine-β-alanine) as a chelating agent examined. Trityl chloride resin was used as a carrier.

http://dx.doi.org/10.5935/0103-5053.20160064

Published online: March 1, 2016

*e-mail: rahimi_rah@iust.ac.ir


Department of Chemistry

 Dr. Rahmatollah Rahimi
  Professor, Inorganic Chemistry Division
  E-mail address: Rahimi_Rah@iust.ac.ir
  Office Tele: 77240290, 77240-50(2718)
  Fax: 77491204

  AWT IMAGE

  Academic Degrees:
  Bachelor of Science: Chemistry, Howard University, USA, 1983
  Master of Science: Physical chemistry, Howard University, USA, 1987
  Ph. D.: Inorganic Chemistry, Howard University, USA, 1991

 Active Research fields:
  - Synthesis and characterization of porphyrins and metalloporphyrins and Investigation of their applications.
  - Photocatalysis process
  - Preparation and characterization of solar cells
  - Invironmental projects
  - Bioinorganic chemistry
  Teaching Experiences:
  A) Teaching Courses at undergraduate level:
  -General chemistry
  -Inorganic Chemistry
  -Physical chemistry
  -Physical chemistry laboratory
  -General Chemistry laboratory
  -Chemistry science literature

  B) Teaching Courses at graduate level (MS):
  -The professional language for Chemistry
  -Inorganic kinetics and Thermodynamics
  -Physical Inorganic Chemistry
  -Research method
  -Advanced Inorganic Chemistry
  -Bio Inorganic Chemistry

  C) Teaching Courses at graduate level (PhD):
  -Advanced Bio Inorganic Chemistry
  -Structures and bonds of inorganic components
  - Organometallic Chemistry
  Research activities:
  A) Scientific Research articles :
  More than 175 Articles Published at Conferences and Journals

  Patent:

1. “Application of LED lamps for treatment and disinfection of wastewaters using nanophotocatalysts” Rahmatollah Rahimi, Javad Shokraian, Mahboobeh Rabbani, 1393
2. “Synthesis of ZnO Nanorods in low temperature via Coprecipitation Method” Rahmatollah Rahimi, Marzieh Yaghoubi Berijani, Solmaz Zargari, 1393

3. “Synthesis of BiVO4 photocatalyst with two monoclinic and tetragonal phases, active in visible and ultraviolet region”, Rahmatollah Rahimi, Marzieh Yaghoubi Berijani, Solmaz Zargari, 1393
   
4. “Synthesis of polypyrrole-iron oxide functionalized with porphyrin as an efficient sorbent of industrial pollutions”, Rahmatollah Rahimi, Meisam Asadi Davati, Solmaz Zargari, 1392

5. “ Synthesis of Titanium dioxide (TiO2)-Vanadium phosphorous nanocomposite oxidized with silver (Ag-VPO) as a catalyst (Ag-VPO/TiO2) and is organic pollution degradation under visible light illumination”, Rahmatollah Rahimi, Masoumeh Mahjoub Moghaddas, Solmaz Zargari, 1391

6. “ Synthesis of SbVO4-TiO2 nanocomposite as a catalysts and its investigation in degradation of organic pollutions under visible light irradiation”, Rahmatollah Rahimi, Masoumeh Mahjoub Moghaddas, Solmaz Zargari, 1391
7. “Synthesis of Titanium dioxide-Bismut vanadat (BiVO4-TiO2) sensitized with porphyrin (TCPP) and its photocatalytic application under visible light irradiation”, Rahmatollah Rahimi, Masoumeh Mahjoub Moghaddas, Solmaz Zargari, 1391

8. “Preparation ofV-TiO2-TCPP and its concurrent application in removal anddegradation of industrial pollutants”, Rahmatollah Rahimi, Masoumeh MahjoubMoghaddas, Solmaz Zargari, 1391
9. “Preparation of Vdoped TiO2 mesoporous and sensitized with porphyrin over SBA-15substrate”, Ahmad Najafian, Masoumeh Mahjoub Moghaddas, Rahmatollah Rahimi, 1391

10. “Preparation ofporphyrin on SBA-15 catalysts”, Mehdi Deilam Kamar, Ahmad najafian, RahmatollahRahimi, 1391.

11. “Nanoporous TiO2solar cell sensitized with tetra(4-carboxyphenyl)porphyrin”, RahmatollahRahimi, Pegah Tvakoli fard, 2010


Image result for Rahmatollah Rahimi




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Monday, 15 August 2016

High Throughput Enzymatic Enantiomeric Excess: Quick-ee

.
High throughput screening techniques (HTS) are fast and efficient alternatives to evaluate enzymatic activities. Here, this technique is applied to obtain enantiomeric excess and conversions values with chiral fluorogenic probes and a non fluorogenic competitor, which was named Quick-ee. The fluorescent signal reveals of the enantioselectivity of the enzyme. Details are presented in the Article High Throughput Enzymatic Enantiomeric Excess: Quick-ee by Maria L. S. de O. Lima, Caroline C. da S. Gonçalves, Juliana C. Barreiro, Quezia Bezerra Cass and Anita Jocelyne Marsaioli on page 319.

http://dx.doi.org/10.5935/0103-5053.20140282


Cover Article
J. Braz. Chem. Soc. 2015, 26(2), 319-324

High Throughput Enzymatic Enantiomeric Excess: Quick-ee

Maria L. S. O. Lima; Caroline C. S. Gonçalves; Juliana C. Barreiro; Quezia B. Cass; Anita J. Marsaioli
Lima MLSO, Gonçalves CCS, Barreiro JC, Cass QB, Marsaioli AJ. High Throughput Enzymatic Enantiomeric Excess: Quick-ee.J. Braz. Chem. Soc. 2015;26(2):319-324
/////////////High Throughput,  Enzymatic,  Enantiomeric Excess,  Quick-ee
http://jbcs.sbq.org.br/imagebank/pdf/v26n2a14.pdf
http://jbcs.sbq.org.br/imagebank/pdf/v26n2a14-Sup01.pdf

Friday, 29 July 2016

Ring-locking enables selective anhydrosugar synthesis from carbohydrate pyrolysis


Ring-locking enables selective anhydrosugar synthesis from carbohydrate pyrolysis

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC01600F, Paper
Li Chen, Jinmo Zhao, Sivaram Pradhan, Bruce E. Brinson, Gustavo E. Scuseria, Z. Conrad Zhang, Michael S. Wong
The nonselective nature of glucose pyrolysis chemistry can be controlled by preventing the sugar ring from opening and fragmenting.

Ring-locking enables selective anhydrosugar synthesis from carbohydrate pyrolysis

*Corresponding authors
aDepartment of Chemical and Biomolecular Engineering, Rice University, Houston, USA
E-mail: mswong@rice.edu
bDepartment of Chemistry, Rice University, Houston, USA
cDalian National Laboratory of Clean Energy, Dalian Institute of Chemical Physics, Dalian, China
E-mail: zczhang@dicp.ac.cn
dDepartment of Civil and Environmental Engineering, Rice University, Houston, USA
eDepartment of Materials Science and NanoEngineering, Rice University, Houston, USA
Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC01600F
The selective production of platform chemicals from thermal conversion of biomass-derived carbohydrates is challenging. As precursors to natural products and drug molecules, anhydrosugars are difficult to synthesize from simple carbohydrates in large quantities without side products, due to various competing pathways during pyrolysis. Here we demonstrate that the nonselective chemistry of carbohydrate pyrolysis is substantially improved by alkoxy or phenoxy substitution at the anomeric carbon of glucose prior to thermal treatment. Through this ring-locking step, we found that the selectivity to 1,6-anhydro-β-D-glucopyranose (levoglucosan, LGA) increased from 2% to greater than 90% after fast pyrolysis of the resulting sugar at 600 °C. DFT analysis indicated that LGA formation becomes the dominant reaction pathway when the substituent group inhibits the pyranose ring from opening and fragmenting into non-anhydrosugar products. LGA forms selectively when the activation barrier for ring-opening is significantly increased over that for 1,6-elimination, with both barriers affected by the substituent type and anomeric position. These findings introduce the ring-locking concept to sugar pyrolysis chemistry and suggest a chemical-thermal treatment approach for upgrading simple and complex carbohydrates.
////////Ring-locking ,  selective anhydrosugar, carbohydrate pyrolysis, synthesis

Tuesday, 19 July 2016

2-chloro-3-(3-chloro-5-iodophenoxy)-4-(trifluoromethyl)pyridine




2-chloro-3-(3-chloro-5-iodophenoxy)-4-(trifluoromethyl)pyridine


1H NMR (400 MHz, DMSO-d6) δ 8.65 (d, J = 4.9 Hz, 1H), 7.95 (t, J = 4.5 Hz, 1H), 7.60 (dd, J = 1.3, 2.9Hz, 1H), 7.38 (br. s., 1H), 7.29 - 7.15 (m, 1H)


13C NMR (101 MHz, DMSO-d6) δ 157.10, 148.02, 145.37, 142.46 (q, JC-F = 2.0 Hz), 135.00, 132.82 (q,JC-F = 33.2 Hz), 131.69, 122.91, 121.59 (q, JC-F = 4.0 Hz), 121.34 (q, JC-F = 273.7 Hz), 115.47, 95.72

19F NMR (377 MHz, DMSO-d6) δ -61.96 (s, 1F)
mp 71.69-79.27 °C






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Monday, 11 July 2016

Nickel-Catalyzed Decarbonylative Suzuki–Miyaura Coupling of Amides To Generate Biaryls

Thumbnail image of graphical abstract








Shi et al. have reported a nickel-catalyzed decarbonylative Suzuki–Miyaura reaction which uses an N-aroylpiperidine-2,6-dione as the coupling partner for the boronic acid ( Angew. Chem., Int. Ed. 2016556959−6963).
The method is attractive from the point of view of the stability of N-aroylpyrrolidine-2,5-diones toward storage and manipulation and the flexibility they add to the chemist’s toolbox, given their preparation from a different group of precursors to aryl halides or triflates.
Notably, the reaction uses an air-stable and inexpensive nickel catalyst, and the reactions tolerate the presence of water. While a standard reaction temperature of 150 °C is quoted, the use of temperatures as low as 80 °C also seem to be possible. Coupling efficiency is reported to be adversely affected when the aromatic rings of both of the coupling partners bear electron-donating substituents.
Ortho substituents on the aromatic rings seem to be beneficial as they facilitate decarbonylation as part of the cross-coupling. Oxidative addition into the N–C(aroyl) bond of the amide is proposed as initiating the catalytic cycle and is possible on account of a reduction in the resonance stabilization of the N-aroyl functionality versus a conventional aromatic amide.

Suzuki–Miyaura Coupling

Synthesis of Biaryls through Nickel-Catalyzed Suzuki–Miyaura Coupling of Amides by Carbon–Nitrogen Bond Cleavage (pages 6959–6963)Shicheng Shi, Guangrong Meng and Prof. Dr. Michal Szostak
Version of Record online: 21 APR 2016 | DOI: 10.1002/anie.201601914
Thumbnail image of graphical abstract
Breaking and making: The first nickel-catalyzed Suzuki–Miyaura coupling of amides for the synthesis of biaryl compounds through N−C amide bond cleavage is reported. The reaction tolerates a wide range of sensitive and electronically diverse substituents on both coupling partners.
STR1
STR1
1H NMR (500 MHz, CDCl3) δ 7.70 (s, 4 H), 7.61 (d, J = 7.3 Hz, 2 H), 7.48 (t, J = 7.6 Hz, 2 H), 7.42 (t, J = 7.3 Hz, 1 H).

STR1
13C NMR (125 MHz, CDCl3) δ 144.87, 139.92, 129.48 (q, J F = 32.5 Hz), 129.13, 128.32, 127.56, 127.42, 125.83 (q, J F = 3.8 Hz), 124.46 (q, J F = 270.0 Hz).

STR1
19F NMR (471 MHz, CDCl3) δ -62.39.



Szostak_PhotoMichal Szostakemail: michal.szostak@rutgers.edu
office: Olson 204
  1. Department of Chemistry, Rutgers University, Newark, NJ, USA

CHEM_BANNER

Research Interests

The central theme of our research is synthetic organic and organometallic chemistry with a focus on the development of new synthetic methods based on transition metal catalysis and various aspects of transition metal mediated free radical chemistry and their application to the synthesis of biologically active molecules.

Selected Publications

  1. Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity and Synthetic Utility. Hu, F.; Patel, M.; Luo, F.; Flach, C.; Mendelsohn, R.; Garfunkel, E.; He, H.; Szostak, M. J. Am. Chem. Soc. 2015137 [doi]
  2. General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically-Controlled Chemoselective N-C Activation. Meng, G.; Szostak, M. Angew. Chem. Int. Ed. 201554[doi]
  3. Aminoketyl Radicals in Organic Synthesis: Stereoselective Cyclization of 5- and 6-Membered Cyclic Imides to 2-Azabicycles using SmI2-H2O. Shi S.; Szostak, M. Org. Lett. 201517, 5144 [doi]
  4. Sterically-Controlled Pd-Catalyzed Chemoselective Ketone Synthesis via N-C Cleavage in Twisted Amides. Meng, G.; Szostak, M. Org. Lett. 201517 [doi]
  5. Recent Developments in the Synthesis and Reactivity of Isoxazoles: Metal Catalysis and Beyond.Hu, F.; Szostak, M. Adv. Synth. Catal. 2015357, 2583. [doi]
  6. Determination of Structures and Energetics of Small- and Medium-Sized One-Carbon Bridged Twisted Amides using ab Initio Molecular Orbital Methods. Implications for Amidic Resonance along the C-N Rotational Pathway. Szostak, R.; Aubé, J.; Szostak, M. J. Org. Chem. 201580, 7905. [doi]
  7. An Efficient Computational Model to Predict Protonation at the Amide Nitrogen and Reactivity along the C-N Rotational Pathway. Szostak, R.; Aubé, J.; Szostak, M. Chem. Commun. 201551, 6395.[doi]
  8. Pd-Catalyzed C-H Activation: Expanding the Portfolio of Metal-Catalyzed Functionalization of Unreactive C-H Bonds by Arene-Chromium π-Complexation. Hu, F.; Szostak, M. ChemCatChem20157, 1061. [doi]
  9. Highly Chemoselective Reduction of Amides (Primary, Secondary and Tertiary) to Alcohols using SmI2/H2O/Amine under Mild Conditions. Szostak, M.; Spain, M.; Eberhart, A. J.; Procter, D. J. J. Am. Chem. Soc. 2014136, 2268. [doi]
  10. Substrate-Directable Electron Transfer Reactions. Dramatic Rate Enhancement in the Chemoselective Reduction of Cyclic Esters using SmI2-H2O: Mechanism, Scope and Synthetic Utility. Szostak, M.; Spain, M.; Choquette, K. A.; Flowers, R. A., II; Procter, D. J. J. Am. Chem. Soc.2013135, 15702. [doi]
  11. Selective Reduction of Barbituric Acids using SmI2-H2O: Synthesis, Reactivity and Structural Analysis of Tetrahedral Adducts. Szostak, M.; Spain, M.; Behlendorf, M; Procter, D. J. Angew. Chem. Int. Ed. 201352, 12559. [doi]
  12. Non-Classical Lanthanide(II) Iodides: Uncovering the Importance of Proton Donors in TmI2-Promoted Electron Transfer. Facile C-N Bond Cleavage in Unactivated Amides. Szostak, M.; Spain, M.; Procter, D. J. Angew. Chem. Int. Ed. 201352, 7237. [doi]
  13. Chemistry of Bridged Lactams and Related Heterocycles. Szostak, M.; Aubé, J. Chem. Rev. 2013,113, 5701. [doi]
For more detail, please see the Szostak Group Web Site 


DSC_0080




GROUP


Prof. Michal Szostak
Assistant Professor
Ph.D., University of Kansas (2009) with Jeffrey Aubé
Postdoctoral, Princeton University (2010) with David MacMillan
Postdoctoral, University of Manchester (2011-2014) with David Procter 
Postdoctoral Researchers
Dr. Feng Hu
Ph.D., Nanjing University, 2009 (Z. Huang)
Postdoctoral, Shanghai Institute of Materia Medica (Y. Hu)
Research Assistant Professor, SIOC (Q. Shen)
Postdoctoral, Lamar University (X. Lei) 
Dr. Pradeep Nareddy
Ph.D., University of Geneva, 2013 (C. Mazet)
Postdoctoral, Leipzig University (C. Schneider) 
Graduate Students
Shicheng Shi
M.S., SIOC, 2013 (R. Wang)
B.S., Nanjing Agriculture University, 2010 
Guangrong Meng
M.S., Fudan University, 2014 (Q. Zhang)
B.S., Dalian Medical University, 2011 
Chengwei Liu
M.S., Soochow University, 2014 (Y. Yao)
B.S., Zaozhuang University, 2011 
Undergraduate Students
Syed Huq (Rutgers, Chemistry, 2014-present)
Marcel Achtenhagen (Rutgers, Chemistry, 2015-present) 
Visiting Students
Yongmei Liu (Yangzhou University, R. Liu)

//////Nickel-Catalyzed,  Decarbonylative Suzuki–Miyaura Coupling,  Amides, Biaryls