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Friday 27 October 2017

1-(Ferrocenyl(phenyl)methyl)pyrrolidine

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1-(Ferrocenyl(phenyl)methyl)pyrrolidine (1b) was obtained (2.14 g, 62% yield) as an orange solid. m.p. 100-102 oC;
1H NMR (400 MHz, CDCl3) δ 7.53 (d, J = 7.6 Hz, 2H), 7.38 (t, J = 7.6 Hz, 2H), 7.29 (t, J = 7.6 Hz, 1H), 4.18 (s, 2H), 4.12 (s, 1H), 4.07 (s, 1H), 3.80 (s, 1H), 3.74 (s, 5H), 2.32 (s, 4H), 1.68 (s, 4H);
13C NMR (100 MHz, CDCl3) δ 128.2, 127.9, 127.0, 71.2, 69.9, 68.6, 68.5, 67.2, 66.4, 54.0, 23.2;
HRMS (ESI) calcd for C21H24FeN+ (M + H)+ 346.1253, found 346.1247.

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Wednesday 25 October 2017

Cross dehydrogenative coupling of N-aryltetrahydroisoquinolines (sp3 C-H) with indoles (sp2 C-H) using a heterogeneous mesoporous manganese oxide catalyst


Cross dehydrogenative coupling of N-aryltetrahydroisoquinolines (sp3 C-H) with indoles (sp2 C-H) using a heterogeneous mesoporous manganese oxide catalyst
Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01919J, Communication
B. Dutta, V. Sharma, N. Sassu, Y. Dang, C. Weerakkody, J. Macharia, R. Miao, A. R. Howell, S. L. Suib
We disclose a novel, heterogeneous catalytic approach for selective coupling of C1 of N-aryltetrahydroisoquinolines with C3 of indoles in the presence of mesoporous manganese oxides.

Cross dehydrogenative coupling of N-aryltetrahydroisoquinolines (sp3 C–H) with indoles (sp2 C–H) using a heterogeneous mesoporous manganese oxide catalyst

Biswanath Dutta

Ph.D Candidate
Chemistry

B.Sc. Chemistry, University of Calcutta, India, 2011
M.S. Chemistry, IIT Bombay, India, 2013
Group Member Since 2013
Research Area: Material synthesis, Catalysis

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Steven Suib

Professor
Emailsteven.suib@uconn.edu
Phone(860) 486-2797
Fax(860) 486-2981
Mailing AddressUniversity of Connecticut
Department of Chemistry
55 N. Eagleville Rd
Storrs, CT 06269
Office LocationCHEM A-313

Abstract

We disclose a novel, heterogeneous catalytic approach for selective coupling of C1 of N-aryltetrahydroisoquinolines with C3 of indoles in the presence of mesoporous manganese oxides. Our work involves a detailed mechanistic investigation of the reaction on the catalyst surface, backed by DFT computational studies, to understand the superior catalytic activity of manganese oxides.

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Tuesday 24 October 2017

4-(quinolin-2-ylsulfonyl)benzonitrile



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4-(quinolin-2-ylsulfonyl)benzonitrile (3ia)5
1H NMR (400 MHz, CDCl3):  = 8.43 (d, J = 8.4 Hz, 1 H), 8.28 – 8.22 (m, 3 H), 8.12 (d, J = 8.4 Hz, 1 H), 7.91 (d, J = 8.4 Hz, 1 H), 7.85 – 7.80 (m, 3 H), 7.70 (t, J = 8.0 Hz, 1 H); 13C NMR (100 MHz, CDCl3): δ = 157.0, 147.4, 143.2, 139.1, 132.7, 131.4, 130.2, 129.8, 129.6, 129.0, 127.8, 117.5, 117.4, 117.2.

Base-free, ultrasound accelerated one-pot synthesis of 2-sulfonylquinolines on water

 

Abstract

Without employing any base and organic solvent, an economical, practical and eco-friendly protocol has been developed for the one-pot synthesis of various functionalized 2-sulfonylquinolines from easily accessible starting materials on water under open-air conditions. Compared with conventional heating conditions, the use of ultrasound techniques not only improves the reaction efficiency and enhances the reaction rate but also minimizes the side reactions. This process has a broad substrate scope, mild reaction conditions, good yields, excellent chemo- and regioselectivity, operational simplicity, ease of scale-up and high energy efficiency. In addition, the process is remarkably greener than previous routes with an atom economy of 70.7%, E-factor of 1.17 and eco-scale score of 71.

Friday 20 October 2017

Ethyl acetate

Ethyl acetate example:

EthylacetateH

Predictions:
PositionIntegrationSplittingChemical Shift
12Three nearest neighbours that are equivalent – quartetSingle bond to oxygen – deshielded
23Two nearest neighbours that are equivalent – tripletSaturated alkyl group far from ester group – shielded
2′3No nearest neighbours – singletAdjacent to the carbon of a carbonyl – slightly deshielded

Ethyl crotonate

ehtylcrotonateblog1



Homonuclear J-resolved Spectroscopy (JRES): An Educational Tool


Many undergraduates that have been introduced to NMR understand the concepts of chemical shift and coupling, however struggle when presented with a real 1H NMR spectrum. For a novice at interpreting proton NMR spectra, it can be difficult to distinguish between separate resonances and multiplets belonging to the same resonance.
‘JRES’ is a 2D homonuclear experiment that produces a J-resolved spectrum, i.e. the chemical shift along one axis (f2) and the proton-proton coupling along the other axis (f1). Essentially, the projection along f2 is a decoupled proton spectrum, which greatly simplifies the spectrum and allows students to quickly identify the chemical shift and coupling pattern.
Comparison of the JRES spectrum with the 1D proton spectrum allows students to understand how proton-proton coupling affects the appearance of the spectrum and become more confident at distinguishing between multiplets and different resonances.



ehtylcrotonateblog2

In the 1D proton NMR spectrum there are a set of peaks around 5.5-6 ppm. It is not obvious to the beginner whether these are two separate resonances or a large doublet. In the JRES we can see that in fact the two resonances collapse into one peak in the f2 dimension and is split into a doublet in the f1 dimension, which means the peaks are one proton split into a doublet. From the 1D proton spectrum it is also difficult to determine whether the set of peaks between 6.3-7.2 ppm is one or multiple resonances, and what the splitting pattern is. This is resolved in the JRES spectrum where again all of the peaks collapse into one in the f2 dimension, so the set of peaks is due to one resonance. It can also be determined by JRES that it is split into a doublet of quartets, which is difficult to see in the 1D proton NMR spectrum.




NMR EXAMPLES

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  • Figure 1Proton NMR of 100% Methyl Acetate


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 2Proton NMR of 100% Methyl Propionate







Proton NMR of 100% Methyl Butyrate






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1H NMR spectra of the C4H8O2 isomers

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