CuI/1,10-Phen/PEG Promoted Decarboxylation of 2, 3-Diarylacrylic

CuI/1,10-Phen/PEG Promoted Decarboxylation of 2, 3-Diarylacrylic acids: Synthesis of Stilbenes under Neutral and Microwave Conditions with in situ Generated Recyclable Catalyst

Yong Zou, *a Qi Huang,a,b Tong-kun Huang,a Qing-chun Ni,c En-sheng Zhang,a,b Tian-long Xu,a,b Mu Yuand

a Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P. R. China b University of Chinese Academy of Sciences, Beijing 100039, P. R. China c Guangzhou General Pharmaceutical Research Institute, Guangzhou 510240, P. R. China d Guangzhou Medical University, Guangzhou 510182, P. R. China

Tel: +86-20-85231309; Fax: +86-20-85231119. E-mail: zou_jinan@163.com

Supporting Materials

Content General .……………………………………….…………………….…………………………1 Drawing of the crystal structure of 2g….………………………………………….…..…...….1 Recyclability of [CuI(1,10-Phen)]2 ……………………………………………………..…...….2 Characterization data of [CuI(1,10-phen)]2………………………….……………...…………2 Spectra for products (1a, 1r and 2a-2s)….…………………………………………………..…7

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

1. General

2,3-Diaryl acrylic acids were directly obtained through Perkin reaction except 1a and 1r.

Other reagents and chromatography grade solvents were obtained from commercial sources and

used without further purification unless otherwise stated. Petroleum ether (PE) used refers to the

boiling fraction of 60–90 ºC. All microwave assisted reactions were carried out with Microwave

Synthesizer (WBFY-205, Gongyi City Yu Hua Instrument Co. Ltd, China), and the reaction

temperature was detected by infrared thermometer. The melting points are uncorrected. 1H NMR

and 13C NMR spectra were measured on a 400 MHz spectrometer (1H 400 MHz, 13C 100 MHz)

using CDCl3 or DMSO-d6 as the solvent at room temperature. Chemical shifts are reported in

parts per million (ppm) and are calibrated using residual undeuterated solvent as an internal

reference. HRMS spectra were recorded on a LC-Q-TOF (ESI) apparatus. The single X-ray

diffraction measurement was performed on X-ray diffractometer. The morphology was

characterized using scanning electron microscopy (SEM, 15 kV). Thermogravimetric analysis

(TGA) was carried out with a heating rate of 3 deg/min in a flowing argon atmosphere.

2. Drawing of the crystal structure of 2g

Figure 1 X-ray crystal structure of 2g

Table S1 Recyclability of [CuI(1,10-Phen)]2

[CuI(1,10-phen)]2 (5 mol%)

MW(800 W, 6 min), PEG-400

Run Catalyst recovery(%) T/min Product yield(%)

1a 87 6 84 2b 86 6 83 3b 85 6 82 4b 85 6 82 5b 85 6 82

a Reaction condition: 1g (50 mmol), [CuI(1,10-phen)]2 (5 mol %) which was recovered from initial reaction, PEG-400 (100 ml), under N2 atmosphere, the mixture was stirred under microwave irradiation (800 W, 180-190 ºC) for 6 min (2-min irradiation each time with a 5-min interval between). b The recovered catalyst was used under identical reaction conditions to those for the first run.

3. Characterization data of [CuI(1,10-phen)]2

1HNMR of [CuI(1,10-phen)]2

1HNMR of 1,10-phen·H2O

IR of [CuI(1,10-phen)]2

IR of 1,10-phen·H2O

TG of [CuI(1,10-phen)]2

MS-FAB of [CuI(1,10-phen)]2

SEM of [CuI(1,10-phen)]2

PXRD of [Cu(1, 10-phen)]2

4. Spectra for products (1a, 1r and 2a-2s)

COOHH3CO

H3COOCH3

H3COOH

Z-3’-animo-3,4,4’,5-tetramethoxystilbene (2a)

Z-3’-hydroxyl-3,4,4’,5-tetramethoxystilbene(2b)

Z-3’-bromo-3,4,4’,5-tetramethoxystilbene (2c)

Z-3’-nitro-3,4,4’,5-tetramethoxystilbene(2d)

Z-3’-bromo-3,4’,5-trimethoxystilbene (2e)

Z-3’-hydroxyl-3,4’,5-trimethoxystilbene (2g)

E-3,4’,5-trihydroxylstilbene (2i)

E-4’-hydroxy-4-methoxylstilbene (2j)

E-4’-hydroxy-3,5-dimethoxylstilbene (2k)

Z-3,4,4’,5-tetramethoxystilbene (2l)

E-3’-animo-3,4,4’,5-tetramethoxystilbene (2m)

E-3’-hydroxyl-3,4,4’,5-tetramethoxystilbene (2n)

4-(5,7-dimethoxybenzofuran-2-yl)phenol (2r-1)

3-(4-hydroxybenzylidene)-5,7-dimethoxybenzofuran-2(3H)-one (2s)

CuI/1,10-Phen/PEG Promoted Decarboxylation of 2, 3-Diarylacrylic

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