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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Iodine Catalyzed xidation of Alcohols and Aldehydes to Carboxylic Acids in Water: A Metal-Free Route to Synthesis of Furandicarboxylic Acid and Terephthalic Acid Susanta Hazra, Mayukh Deb, and Anil. J. Elias * Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi eliasanil@gmail.com
2 Contents 1. General information...s3 2. Effect of catalysts on the C-H oxidation (Table S1)....S4 3. Effect of amount of catalyst loading for the oxidation reaction (Table -S2)...S5 4. Effect of oxidant used for the reaction (Table-S3)......S5 5. Effect of amount of oxidant used for oxidation reaction (Table-S4)...S6 6. ptimization of reaction conditions for oxidation of aldehyde (Table-S5) S6 7. Effect of base, solvent and temperature used for the reaction (Table- S5)...S7 8. General procedure for oxidation of alcohols and aldehydes...s8 9. Gram scale/ one pot synthesis of FDCA and Terephthalic acid...s8-s9 10. References...S Identification of products, 1 H and 13 C{ 1 H} NMR data...s11-s H and 13 C{ 1 H} NMR spectra of prepared compounds...s18-s58 S2
3 General Information Unless otherwise stated, all reactions were performed under open atmosphere. 1 H and 13 C NMR spectra were recorded on a Bruker Spectrospin DPX-300 NMR spectrometer at 300 and MHz, respectively. All chemical shifts (δ) are reported in ppm and coupling constants (J) in Hz. All chemical shifts are related to residual solvent peaks [CDCl 3 : 7.26 ( 1 H), ( 13 C); DMS-d 6 : 2.50 ( 1 H), ( 13 C)]. All alcohols and aldehydes were purchased from commercial sources and hydroxymethylfurfural (HMF) was prepared according to literature procedure. [1] Deionised water, TBHP (70% in water), iodine and NaH were used as received. S3
4 Experimental Section: Table S1: Effect of catalysts on the C-H oxidation. Me H H H Catalyst TBHP(70% in water) 4 equiv. NaH (20 mol%), H 2 70 o C, 10-16h Me H Entry No. Catalyst % of yield (isolated) I KI 48 4 NaI 46 5 TBAI 15 6 TBAB 0 S4
5 Table S2: Effect of amount of catalyst loading for the oxidation reaction. Me H H H I 2 (X mol%) TBHP (70% in water) 4 equiv. NaH (20 mol%), H 2 70 o C, 10-16h Me H Entry No. Amount of I 2 ( X mol%) % of yield (isolated) Table S3: Effect of oxidant used for the reaction. Me H H H I 2 (10 mol%) xidant NaH (20 mol%), H 2 70 o C, 10-16h Me H Entry No. xidant % of yield (isolated) aq. TBHP H DTBP 0 6 K 2 S NM 0 S5
6 Table S4: Effect of amount of oxidant used for oxidation reaction Me H H H I 2 (10 mol%) aq. TBHP(x equiv.) NaH (20 mol%), H 2 70 o C, 10-16h Me H Entry No. aq. TBHP (x equiv.) % of yield (isolated) a a. Since the TBHP used was 70% in water, it is equivalent to 2.8 equivalent of pure TBHP. 90 Table S5: ptimization of reaction conditions for oxidation of aldehyde H I 2 / NaH H aq. TBHP H 2, 70 o C 10h Entry No Iodine ( X mol%) aq. TBHP (Y equiv.) NaH (Z mol%) Reaction temperature/ o C Yield (isolated) S6
7 Table S6: Effect of base, solvent and temperature used for the reaction Entry No. Base (20mol%) Solvent 1 NaH H 2 Tempereture / o C RT 0 2 NaH H NaH H a NaH H KH H Na 2 C 3 H K 2 C 3 H H % ofyield (isolated) 9 NaAc H KAc H NaH DMS NaH DCM NaH 1,4 dioxane NaH CH 3 CN NaH tert-butanol a. Reaction was also carried out with 1 equiv. of NaH at 100 o C with yield of 90%. General procedure for oxidation of alcohols S7
8 A 15 ml screw capped vial was charged with a magnetic bead, 5 mmol of alcohol, 0.5 mmol (10 mol%) of I 2 and 20 mmol (4 equiv.) of aq. TBHP (70% in H 2 ). Afterwards, 1 mmol (20 mol%) of NaH with additional 2 ml of deionized water (ph = 10) were added to the reaction mixture and it was heated at 70 o C for h. Afterwards, the reaction mixture was neutralized by aq. HCl and extracted with EtAc and aq. Na 2 S 2 3 solution. The organic layer was dried over anhydrous Na 2 S 4 and after evaporation of the solvent analytically pure carboxylic acids were obtained. [2,3] General procedure for oxidation of aldehydes A 15 ml screw capped vial was charged with a magnetic bead, 5 mmol of aldehyde, 0.5 mmol (10 mol%) of I 2 and 20 mmol (4 equiv.) of aq. TBHP. Afterwards, 1 mmol (20 mol%) of NaH with additional 2 ml of deionized water (ph =10) were added to the reaction mixture and it was heated at 70 o C for h. Afterwards, the reaction mixture was neutralized by aq. HCl and extracted with EtAc and aq. Na 2 S 2 3 solution. The organic layer was dried over anhydrous Na 2 S 4 and after evaporation of the solvent analytically pure carboxylic acids were obtained. [2,3] Gram scale synthesis of FDCA from HMF A 1000 ml of round bottom flask was charged with a magnetic bead, mmol (10 gm) of HMF, mmol (20 mol%) of I 2 and 634 mmol (8 equiv.) of aq. TBHP. Afterwards, mmol (50 mol%) of NaH with additional 100 ml of H 2 were added to the reaction mixture and it was heated at 70 o C for 36 h. Afterwards, the reaction mixture was neutralized by aq. HCl and extracted with EtAc and aq. Na 2 S 2 3 solution. The organic layer was dried over anhydrous Na 2 S 4 and after evaporation of the solvent analytically pure FDCA was obtained in 53% yield (6.55 gm). [2,4] ne pot synthesis of FDCA from D-fructose S8
9 To a 150 ml flask equipped with stirrer bars, D-fructose (4.5 g, 25 mmol), isopropyl alcohol (50 ml), and hydrochloric acid (12.5m aqueous solution, 0.1 ml) were added. The reaction flask was heated on an oil bath to 120 o C with stirring. The reaction was stopped after 4 h and the mixture was filtrated to remove insoluble humin by-product. Solvent in the reaction mixture was then evaporated and dried to give the crude HMF product (3.15 gm). Afterwards, I 2 (5 mmol), aq. TBHP (200 mmol, 8 equiv.), NaH (12.5 mmol) and H 2 (50 ml) were added and the reaction mixture was stirred at 70 o C for 36h. Afterwards, the reaction mixture was neutralized by aq. HCl and extracted with EtAc and aq. Na 2 S 2 3 solution. The organic layer was dried over anhydrous Na 2 S 4 and after evaporation of the solvent FDCA was obtained in 41% yield (1.61 gm). Gram scale synthesis of Terephthalic acid A 100 ml of round bottom flask was charged with a magnetic bead, mmol (2 gm) of 1, 4-benzenedimethanol, 2.89 mmol (20 mol%) of I 2 and mmol (8 equiv.) of aq. TBHP. Afterwards, 7.24 mmol (50 mol%) of NaH with additional 10 ml of H 2 were added to the reaction mixture and it was heated at 70 o C for 36 h. Afterwards, the reaction mixture was neutralized by aq. HCl and extracted with EtAc and aq. Na 2 S 2 3 solution. The organic layer was dried over anhydrous Na 2 S 4 and after evaporation of the solvent analytically pure terephthalic was obtained. [3] References: S9
10 [1] L. Lai, Y. Zhang, ChemSusChem 2011, 4, [2] M. S. Ahmed, D.S. mannel, T. W. Root, S. S. Stahl, rg. Process Res. Dev. 2017, DI: /acs.oprd.7b [3] A. Sarbajna, I. Dutta, P. Daw, S. Dinda, S. M. W. Rahaman, A. Sarkar, J. K. Bera, ACS Catal. 2017, 7, [4] N. Jiang, B. You, R. Boonstra, I. M. T. Rodriguez, Y. Sun, ACS Energy Lett. 2016, 1, Identification of products: S10
11 Compound 1 H Me 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, 1H), (d, J= 9Hz, 2H), (d, J= 9Hz, 2H), 3.88 (s, 3H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , , , Compound 2 H 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, 1H), 8.16 (m, J= 9Hz, 2H), 7.55 (t, 1H), 7.50 (t, 2H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , , Compound 3 2 N H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (d, J= 6Hz, 2H), (d, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 4 S11
12 H H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), 10.24(s, 1H), (d, J= 9Hz, 2H), (d, J= 9Hz, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 5 Me H 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, 1H), 7.91 (d, J= 9Hz, 2H), (d, J= 9Hz, 2H), 2.34 (s, 3H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , , , Compound 6 Cl H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (d, J= 9Hz, 2H), (d, J= 12Hz, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 7 Br H S12
13 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (d, J= 9Hz, 2H), (d, J= 12Hz, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 8 F H 1 H-NMR (CDCl 3, 300 MHz): (m, 2H), 7.15 (m, 2H); 13 C-NMR (CDCl 3, 75 MHz): 171.5, 166.7, 133.2, (d, J = 2.6 Hz), 116.1; 19 F-NMR (CDCl 3 ): (s, 1F). Compound 9 F 3 C H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (d, J= 9Hz, 2H), (d, J= Hz, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 10 NC H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (d, J= 9Hz, 2H), (d, J= 9Hz, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , , , S13
14 Compound 11 H Me 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, 1H), 7.80 (s, 1H), (m, 3H), 2.27 (s, 3H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , , , , Compound 12 H N 2 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (m, 4H); 13 C-NMR (DMSd 6, 75 MHz, ppm): , , , , Compound 13 Me H Me Me 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), 6.90 (s, 2H), (m, 9H); 13 C- NMR (CDCl 3, 75 MHz, ppm): , , , , 21.45, Compound 14 Cl Cl H S14
15 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), 7.64(t, 1H), (m, 2H); 13 C- NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 15 F F H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), 7.63(t, 1H), (m, 2H); 13 C- NMR (DMS-d 6, 75 MHz, ppm): , , , , Compound 16 H 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, 1H), 7.57 (s, 1H), 7.27 (s, 1H), 6.48 (s, 1H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , , Compound 17 S H 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, 1H), 7.82 (d, 1H), 7.56 (d, 1H), 7.06 (s, 1H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , , Compound 18 N H S15
16 1 H-NMR (DMS-d 6, 300 MHz, ppm): (br, 1H), (d, J= 9Hz, 2H), (d, 2H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , , Compound 19 H H 1 H-NMR (DMS d 6, 300 MHz, ppm): 8.04 (s, 4H), (br, s, 2H); 13 C-NMR (DMS d 6, 75 MHz, ppm): , , Compound 20 H H 1 H-NMR (DMS-d 6, 300 MHz, ppm): 7.30 (s, 2H), 13 C-NMR (DMS-d 6, 75 MHz, ppm): , , Compound 21 H 1 H-NMR (CDCl 3, 300 MHz, ppm): (m, 5H), 3.66 (s, 2H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , , , 128.6, , Compound 22 H S16
17 1 H-NMR (CDCl 3, 300 MHz, ppm): (s, 1H), 2.35 (t, J = 7.4 Hz, 2H), 1.68 (m, 2H), 1.00 (t, J = 7.5 Hz, 3H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , 36.00, 18.72, Compound 23 H 1 H-NMR (CDCl 3, 300 MHz, ppm): (s, 1H), 2.35 (t, J = 7.4 Hz, 2H), 1.68 (m, 2H), 1.00 (m, J = 7.5 Hz, 2H), 0.98 (t, 3H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , 26.00, 23.78, 18.75, Compound 24 ( ) 6 H 1 H-NMR (CDCl 3, 300 MHz, ppm): (br, s, 1H), 2.34 (t, J = 7.7 Hz, 2H), 1.61 (m, 2H), 1.29 (m, 8H), 0.88 (m, 3H); 13 C-NMR (CDCl 3, 75 MHz, ppm): , 34.3, 31.9, 29.2, 29.1, 25.9, 22.30, Compound 25 H H 1 H-NMR (DMS-d 6, 300 MHz, ppm): (b, 2H), 2.43 (m, 4H); 13 C-NMR (DMS-d 6, 75 MHz, ppm): , H- NMR (in CDCl 3 ) spectra of compound 1 S17
18 13 C{H 1 }- NMR (in CDCl 3 ) spectra of compound 1 S18
19 1 H- NMR (in DMS-d 6 ) spectra of compound 3 S19
20 S20
21 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 3 S21
22 1 H- NMR (in DMS-d 6 ) spectra of compound 4 S22
23 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 4 S23
24 1 H- NMR (in CDCl 3 ) spectra of compound 5 S24
25 13 C{H 1 }- NMR (in CDCl 3 ) spectra of compound 5 S25
26 1 H- NMR (in DMS-d 6 ) spectra of compound 6 S26
27 1 H- NMR (in DMS-d 6 ) spectra of compound 7 S27
28 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 7 S28
29 1 H- NMR (in DMS-d 6 ) spectra of compound 9 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 9 S29
30 19 F- NMR (in DMS-d 6 ) spectra of compound 9 S30
31 1 H- NMR (in DMS-d 6 ) spectra of compound 9 S31
32 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 10 S32
33 S33
34 1 H- NMR (in CDCl 3 ) spectra of compound 11 S34
35 13 C{H 1 }- NMR (in CDCl 3 ) spectra of compound 11 1 H- NMR (in DMS-d 6 ) spectra of compound 12 S35
36 1 H- NMR (in DMS-d 6 ) spectra of compound 13 S36
37 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 13 S37
38 S38
39 1 H- NMR (in DMS-d 6 ) spectra of compound 15 S39
40 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 15 S40
41 19 F- NMR (in DMS-d 6 ) spectra of compound 15 S41
42 1 H- NMR (in CDCl 3 ) spectra of compound 16 S42
43 13 C{H 1 }- NMR (in CDCl 3 ) spectra of compound 16 S43
44 1 H- NMR (in CDCl 3 ) spectra of compound 17 S44
45 13 C {H 1 }- NMR (in CDCl 3 ) spectra of compound 17 S45
46 1 H- NMR (in DMS-d 6 ) spectra of compound 18 S46
47 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 18 S47
48 1 H- NMR (in DMS-d 6 ) spectra of compound 19 S48
49 1 H- NMR (in DMS-d 6 ) spectra of compound 20 S49
50 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 20 S50
51 1 H- NMR (in DMS-d 6 ) spectra of compound 21 S51
52 13 C{H 1 }- NMR (in DMS-d 6 ) spectra of compound 21 S52
53 13 C{H 1 }- NMR (in CDCl3) spectra of compound 24 S53
54 1 H- NMR (in DMS-d 6 ) spectra of compound 25 S54
55 13 C{H 1 }- NMR (in CDCl3) spectra of compound 25 S55
56 1 H- NMR (in CDCl 3 ) spectra of HMF S56
57 13 C{H 1 }- NMR (in CDCl3) spectra of HMF S57
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Phenazine, -dioxide scaffold as selective hypoxic cytotoxin pharmacophore. Structural modifications looking for further DA topoisomerase II-inhibition activity Mariana Gonda, Marcos ieves, Elia unes, Adela
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Electronic upplementary Material (EI) for RC Advances This journal is The Royal ociety of Chemistry 2013 BA-15 functionalized sulfonic acid confined hydrophobic and acidic ionic liquid: a highly efficient
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Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry
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Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Catalyst-Free and Solvent-Free ydroboration of Aldehydes. Stachowiak,
An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
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Poly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction
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Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
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Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Synthesis of cyclic carbonates from diols and C 2 catalyzed by carbenes Felix D. Bobbink,* Weronika
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Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany rganocatalytic Conjugate Addition of Malonates to a,ß-unsaturated Aldehydes: Asymmetric Formal Synthesis of (-)-Paroxetine, Chiral Lactams
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Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong
Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides
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Supporting Information. for. Synthetic routes to [Au(NHC)(OH)] (NHC = N- heterocyclic carbene) complexes
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Supporting Information for Synthetic routes to [Au(HC)(OH)] (HC = - heterocyclic carbene) complexes Adrián Gómez-Suárez, Rubén S, Alexandra M. Z. Slawin and Steven P. olan* EaStChem School of chemistry,
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Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
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Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,
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Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supporting Information Lithium Triethylborohydride-Promoted Generation of α,α-difluoroenolates
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
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Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe
Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline
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Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal
Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
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Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 205 A simple and greener approach
Tuning Porosity and Activity of Microporous Polymer Network Organocatalysts by Co-Polymerisation
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Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
SBA-15-functionalized sulfonic acid confined acidic ionic liquid: a powerful and water-tolerant catalyst for solvent-free esterifications
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How to build and race a fast nanocar Synthesis Information
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Heterogeneously catalyzed selective aerobic oxidative cross-coupling of terminal alkynes and amides with simple copper(ii) hydroxide
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Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
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Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some
Supporting Information
Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a
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Supporting nformation for Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes Hao Wang 1, Cui Chen
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Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W.
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Data for: Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes
Oxidation of 5-hydroxymethylfurfural to maleic anhydride with molecular oxygen
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Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using
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Supporting Information Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers Jian-Bo Liu, Xiu-Hua Xu, and Feng-Ling Qing Table of Contents 1. General Information --------------------------------------------------------------------------2
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Supporting Information An L-proline Functionalized Metallo-organic Triangle as Size-Selective Homogeneous Catalyst for Asymmertry Catalyzing Aldol Reactions Xiao Wu, Cheng He, Xiang Wu, Siyi Qu and Chunying
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Dynamic covalent templated-synthesis of [c2]daisy chains. Altan Bozdemir, a Gokhan Barin, a Matthew E. Belowich, a Ashish. Basuray, a Florian Beuerle, a and J. Fraser Stoddart* ab a b Department of Chemistry,
Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.
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Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 208 Supplementary Information Stabilisation
Reactive fluorescent dye functionalized cotton fabric as a Magic Cloth for selective sensing and reversible separation of Cd 2+ in water
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2015 Supplementary Information Reactive fluorescent dye functionalized cotton
Metal-Free Oxidative Cleavage of C-C bond in α-hydroxy-βoxophosphonates
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 25 Supporting Information Metal-Free xidative Cleavage of C-C bond in α-hydroxy-βoxophosphonates
Experimental details
Supporting Information for A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyx) ligand Hideki Shimizu 1,2, Jeffrey C. Holder 1 and Brian M. Stoltz* 1 Address:
Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable
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Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2019 Supporting Information Difluorocarbene-derived trifluoromethylselenolation of benzyl halides Xin-Lei
Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
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PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions
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Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles
Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu
A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour
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Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System
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A Photocleavable Linker for the Chemoselective Functionalization of Biomaterials
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Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for I 2 TBHP-catalyzed one-pot highly
Fluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium
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Supplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes
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Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
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Syntheses of a pillar[4]arene[1]quinone and a difunctionalized. pillar[5]arene by partial oxidation. Electronic Supplementary Information (11 pages)
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Syntheses of a pillar[4]arene[1]quinone and a difunctionalized pillar[5]arene by partial oxidation Chengyou an, Zibin Zhang, Guocan Yu and Feihe uang* Department of Chemistry, Zhejiang University, angzhou