Name: 527-21-9|Tetrafluoro-1,4-benzoquinone|98%
Brand: Ambeed
SKU: A960703
Price: 16.0 USD
Availability: InStock
Rating: 91 (30 reviews)

1
[ 527-21-9 ]
[ 771-63-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 2,5-dihydrotoluene In toluene at 30℃; for 15h;
	With diethyl ether; nickel Hydrogenation;
	With toluene; platinum Hydrogenation;

With hydrogen In diethyl ether Ambient temperature;

Reference： [1]Baschieri, Andrea; Amorati, Riccardo; Valgimigli, Luca; Sambri, Letizia [Journal of Organic Chemistry, 2019, vol. 84, # 21, p. 13655 - 13664]
[2]Nield,E.; Taltow,J.C. [Tetrahedron, 1960, vol. 8, p. 38 - 41]
[3]Wallenfels; Draber [Chemische Berichte, 1957, vol. 90, p. 2819,2831]
[4]Nield,E.; Taltow,J.C. [Tetrahedron, 1960, vol. 8, p. 38 - 41]

2
[ 771-63-1 ]
[ 527-21-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With ammonium cerium(IV) nitrate at 20℃; for 1h;
	With lead dioxide
	With ammonium cerium(IV) nitrate

	With cerium(IV) perchlorate In perchloric acid
65 %Chromat.	With oxygen In chloroform; water at 20℃; for 3h;
	With [Ru^III(OH)(2,6-bis{1,1-bis(2-pyridyl)ethyl}pyridine)](PF₆)₂ In aq. buffer at 23.84℃;

Reference： [1]Essers, Michael; Haufe, Guenter [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 23, p. 2719 - 2728]
[2]Wallenfels; Draber [Chemische Berichte, 1957, vol. 90, p. 2819,2831]
[3]Perrier, Serge; Sankararaman, Seth; Kochi, Jay K. [Journal of the Chemical Society. Perkin transactions II, 1993, # 5, p. 825 - 837]
[4]Dziegiec; Grzejdziak [Russian Journal of General Chemistry, 1997, vol. 67, # 1, p. 116 - 119]
[5]Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke; Kobayashi, Shu [Angewandte Chemie - International Edition, 2008, vol. 47, # 42, p. 8093 - 8095]
[6]Ohzu, Shingo; Ishizuka, Tomoya; Kotani, Hiroaki; Kojima, Takahiko [Chemical Communications, 2014, vol. 50, # 95, p. 15018 - 15021]

3
[ 527-21-9 ]
[ 62-53-3 ]
[ 1425-96-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium acetate; acetic acid In ethanol; water at 110℃; for 5h; Inert atmosphere;
88%	Stage #1: 2,3,5,6-tetrafluoro-1,4-benzoquinone With sodium acetate; acetic acid In ethanol; water Inert atmosphere; Glovebox; Stage #2: aniline In ethanol; water at 110℃; for 5h;
	In diethyl ether

Reference： [1]Park, Jesse G.; Jeon, Ie-Rang; Harris, T. David [Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369]
[2]Park, Jesse G.; Jeon, Ie-Rang; Harris, T. David [Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369]
[3]Nield,E.; Taltow,J.C. [Tetrahedron, 1960, vol. 8, p. 38 - 41]

4
[ 527-21-9 ]
[ 22042-73-5 ]
[ 82352-96-3 ]

Yield	Reaction Conditions	Operation in experiment
47%	With cesium fluoride In acetonitrile for 10h; Heating;

Reference： [1]Lindsey, Jonathan S.; Mauzeral, David C. [Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4498 - 4500]

5
[ 527-21-9 ]
[ 771-64-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium hydroxide In 1,4-dioxane; water at 20℃; for 2h;
30.1%	With sodium hydroxide In 1,4-dioxane at 20℃; for 3h;
	With sodium hydroxide In 1,4-dioxane

Reference： [1]Reed, William R.; Dunstan, Maja A.; Gable, Robert W.; Phonsri, Wasinee; Murray, Keith S.; Mole, Richard A.; Boskovic, Colette [Dalton Transactions, 2019, vol. 48, # 41, p. 15635 - 15645]
[2]Murase, Ryuichi; Abrahams, Brendan F.; D'Alessandro, Deanna M.; Davies, Casey G.; Hudson, Timothy A.; Jameson, Guy N. L.; Moubaraki, Boujemaa; Murray, Keith S.; Robson, Richard; Sutton, Ashley L. [Inorganic Chemistry, 2017, vol. 56, # 15, p. 9025 - 9035]
[3]Wallenfels,K.; Friedrich,K. [Chemische Berichte, 1960, vol. 93, p. 3070 - 3082]

6
[ 6669-03-0 ]
[ 527-21-9 ]
[ 41481-22-5 ]
2,3,4,4,5-Pentafluoro-6-(2,2,2-trifluoro-ethoxy)-cyclohexa-2,5-dienone [ No CAS ]
2,3,4,4,6-Pentafluoro-5-(2,2,2-trifluoro-ethoxy)-cyclohexa-2,5-dienone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 14% 2: 13% 3: 35% 4: 14 % Spectr.	With xenon difluoride; hydrogen fluoride at 20 - 22℃; for 0.333333h; Title compound not separated from byproducts;
1: 14 % Spectr. 2: 14 % Spectr. 3: 13 % Spectr. 4: 35 % Spectr.	With xenon difluoride; hydrogen fluoride at 20 - 22℃; for 0.333333h; Further byproducts given. Title compound not separated from byproducts;
1: 35 % Spectr. 2: 14 % Spectr. 3: 13 % Spectr. 4: 14 % Spectr.	With xenon difluoride; hydrogen fluoride at 20 - 22℃; for 0.333333h; Title compound not separated from byproducts;

Reference： [1]Frohn; Bardin [Zeitschrift fur Naturforschung, B: Chemical Sciences, 1996, vol. 51, # 7, p. 1015 - 1021]
[2]Frohn; Bardin [Zeitschrift fur Naturforschung, B: Chemical Sciences, 1996, vol. 51, # 7, p. 1015 - 1021]
[3]Frohn; Bardin [Zeitschrift fur Naturforschung, B: Chemical Sciences, 1996, vol. 51, # 7, p. 1015 - 1021]

7
[ 700-17-4 ]
[ 527-21-9 ]
2,3,5,6-Tetrafluoro-4-(2,3,5,6-tetrafluoro-phenylimino)-cyclohexa-2,5-dienone [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1997,vol. 67,p. 116 - 119

8
[ 3978-81-2 ]
[ 527-21-9 ]
2,3-difluoro-5-oxy-6-(4'-tert-butylpyridinium-1'-yl)-1,4-benzoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In diethyl ether at 20℃; for 8h;

Reference： [1]Koch, Andrew S.; Harbison, Warren Grant; Hubbard, Joshua M.; De Kort, Martin; Roe, Barbara A. [Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5959 - 5963]

9
[ 563-79-1 ]
[ 527-21-9 ]
2,3,5,6-tetrafluoro-4-(1,1,2-trimethyl-allyloxy)-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In benzene-d6 at 20℃; for 2h; Irradiation;

Reference： [1]Kokubo, Ken; Masaki, Takayoshi; Oshima, Takumi [Organic Letters, 2000, vol. 2, # 13, p. 1979 - 1981]

10
[ 4914-92-5 ]
[ 527-21-9 ]
[ 771-63-1 ]
4-(1,3-Dimethyl-2-methylene-butoxy)-2,3,5,6-tetrafluoro-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 19% 2: 33%	In benzene-d6 at 20℃; for 5h; Irradiation;

Reference： [1]Kokubo, Ken; Masaki, Takayoshi; Oshima, Takumi [Organic Letters, 2000, vol. 2, # 13, p. 1979 - 1981]

11
[ 527-21-9 ]
[ 403-41-8 ]
[ 771-63-1 ]
[ 403-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With [(Ph₄Cp-OH)Ru(CO)2]2 In benzene-d6 at 70℃;

Reference： [1]Johnson, Jeffrey B.; Baeckvall, Jan-E. [Journal of Organic Chemistry, 2003, vol. 68, # 20, p. 7681 - 7684]

12
[ 616885-86-0 ]
[ 527-21-9 ]
2,5-bis-{6-[ethyl-(2-methoxy-benzyl)-amino]-hexylamino}-3,6-difluoro-[1,4]benzoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In diethyl ether at 20℃; for 1h;	35 EXAMPLE 35 2,5-bis-{6-[ethyl-(2-methoxy-benzyl)-amine]-hexylamine}-3,6-difluorine-[1,4]benzoquinone (35) A suspension of tetrafluorine-[1,4]benzoquinone (100 mg; 0.56 mmol) in 2 ml of ether is added dropwise to a solution of N1-ethyl-N1-(2-methoxybenzyl)-1,6-hexanediamine (1.23 g; 4.66 mmol) in 3 ml of ethyl ether. The solution immediately becomes a dark red colour. It is left under agitation at room temperature for one hour and all the solvent is evaporated under vacuum. The residue obtained is purified using flash chromatography. Elution with CH2Cl2/MeOH/NH3 aqueous 28% (9:1:0.05) provides the compound 35 in the form of a greenish oil with a yield of 90%. 1H NMR (free base, CDCl3) δ: 1.08 (t, 6H); 1.23-1.63 (m complex, 16H); 2.46-2.64 (m, 8H); 3.51 (q, 4H); 3.64 (s, 4H); 6.17 (br s exchangeable with D2O, 2H); 6.87 (d, 2H); 6.95 (t, 2H); 7.24 (t, 2H); 7.43 (d, 2H).
	In diethyl ether at 20℃; for 1h;

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF BOLOGNA - US2009/93521, 2009, A1 Location in patent: Page/Page column 14
[2]Bolognesi, Maria Laura; Banzi, Rita; Bartolini, Manuela; Cavalli, Andrea; Tarozzi, Andrea; Andrisano, Vincenza; Minarini, Anna; Rosini, Michela; Tumiatti, Vincenzo; Bergamini, Christian; Fato, Romana; Lenaz, Giorgio; Hrelia, Patrizia; Cattaneo, Antonino; Recanatini, Maurizio; Melchiorre, Carlo [Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4882 - 4897]

13
[ 527-21-9 ]
[ 564480-29-1 ]
C₆F₄O₂*2C₉H₆N₂S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In dimethyl sulfoxide; acetonitrile at 20℃;

Reference： [1]Murata, Tsuyoshi; Morita, Yasushi; Yakiyama, Yumi; Fukui, Kozo; Yamochi, Hideki; Saito, Gunzi; Nakasuji, Kazuhiro [Journal of the American Chemical Society, 2007, vol. 129, # 35, p. 10837 - 10846]

14
[ 771-61-9 ]
[ 527-21-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With [Fe(IV)(O)(N-benzyl-N,N',N'-tris(2-pyridylmethyl)-1,2-diaminoethane)]⁽²⁺⁾ In water; acetonitrile at 24.84℃;
	With air for 3.5h; UV-irradiation;

Reference： [1]Jana, Rahul Dev; Munshi, Sandip; Paine, Tapan Kanti [Dalton Transactions, 2021, vol. 50, # 16, p. 5590 - 5597]
[2]Ravichandran, Lakshiminarasimhan; Selvam, Kaliyamoorthy; Swaminathan, Meenakshisundaram [Australian Journal of Chemistry, 2007, vol. 60, # 12, p. 951 - 956]

15
[ 938-63-6 ]
[ 527-21-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With nitric acid In water at 100℃;	1; S1300 Specific operation oxidation step is as follows: Compound D 1eq added to an aqueous solution containing nitric acid 9eq nitric acid, slowly heated to 100 °C, to initiate the reaction, TLC to monitor the reaction. After completion of the reaction was cooled, water was added to precipitate solid was filtered to give compound E, yield 96%.
	With nitric acid heating;
	With HNO₃ heating;

Reference： [1]Current Patent Assignee: BEIJING SINEVA TECHNOLOGY CO LTD - CN106146346, 2016, A Location in patent: Paragraph 0056
[2]Brooke, G. M.; Forbes, E. J.; Richardson, R. D.; Stacey, M.; Tatlow, J. C. [Journal of the Chemical Society][Journal of the Chemical Society, 1965, p. 2088 - 2094]
[3][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.7, 1, page 1 - 84]

16
[ 12126-50-0 ]
[ 527-21-9 ]
[Fe(Cp*)2][fluoranil]2 [ No CAS ]

Reference： [1]Dalton Transactions,2011,vol. 40,p. 9221 - 9228

17
[ 527-21-9 ]
[ 99-57-0 ]
[ 1451044-41-9 ]

Yield	Reaction Conditions	Operation in experiment
38.5%	With sodium acetate In ethanol for 24h;	4 4.2.4 8-Nitro-1,2,4-trifluoro-3H-phenoxazin-3-one (6a) 4.2.4 8-Nitro-1,2,4-trifluoro-3H-phenoxazin-3-one (6a) The title compound was prepared from p-fluoranil 11a (1.51 g, 8.39 mmol) and 2-amino-4-nitrophenol 9 (1.27 g, 8.22 mmol) according to the general procedure. The precipitate was taken into EtOAc (100 mL) and the resulting mixture filtered through a sintered funnel. The insoluble residue was washed several times with EtOAc and discarded. The combined organic filtrates were washed with 10% aq NaOH solution (4100 mL) and water (1100 mL), and dried (MgSO4). The solvent was removed under reduced pressure and the residue subjected to column chromatography, eluting with a gradient mixture of petroleum ether 60-80 °C/Et2O (50:50-0:100). Compound 6a was isolated as a red solid (0.94 g, 3.17 mmol, 38.5%). An orange crystalline solid of 6a was obtained from glacial acetic acid, mp: 212-214 °C; (found: C, 48.6; H, 1.05; N, 9.1%. C12H3F3N2O4 requires C, 48.7; H, 1.0; N, 9.5%); νmax/cm-1 3093 (C-H), 1648 (C=O), 1608 (C=C), 1518 and 1308 (NO2), 1004 (C-F); δH (300 MHz, THF-d8) 6.03 (1H, d, J=9.3 Hz, 6-H), 6.80 (1H, dd, J=9.0, 2.7 Hz, 7-H), 7.06 (1H, d, J=2.7 Hz, 9-H); δC (75 MHz, THF-d8) 115.4 (CH, 6-C), 123.8 (CH, 9-C), 126.2 (CH, 7-C), 129.9 (quat, ddd, J=9.6, 5.1, 1.3 Hz, 10a-C), 130.2 (quat, 9a-C), 136.0 (quat, dd, J=262.4, 6.5 Hz, 4-C), 141.3 (quat, dt, J=272.7, 6.9 Hz, 2-C), 142.2 (quat, dd, J=273.9, 12.0 Hz, 1-C), 140.8 (quat, ddd, J=18.3, 5.5, 1.1 Hz, 4a-C), 143.4 (quat, 8-C), 145.3 (quat, d, J=1.6 Hz, 5a-C), 166.8 (quat, td, J=21.0, 5.6 Hz, 3-C); δF (282 MHz, THF-d8) -282.05 (1F, t, J=2.8 Hz, 4-F), -271.73 (1F, dd, J=9.6, 1.7 Hz, 2-F), -266.07 (1F, dd, J=9.3, 2.5 Hz, 1-F); δH (300 MHz, DMSO-d6) 7.93 (1H, d, J=9.0 Hz, 6-H), 8.56 (1H, dd, J=9.0, 2.4 Hz, 7-H), 8.76 (1H, d, J=2.4 Hz, 9-H); δC (75 MHz, DMSO-d6) 118.4 (CH, 6-C), 125.9 (CH, 9-C), 129.0 (CH, 7-C), 132.1 (quat, 9a-C), 132.5 (quat, dd, J=8.8, 5.2 Hz, 10a-C), 137.8 (quat, dd, J=256.3, 6.45 Hz, 4-C), 143.2 (quat, dt, J=267.75, 6.8 Hz, 2-C), 144.2 (quat, dd, J=270.4, 11.9 Hz, 1-C), 142.8 (quat, d, J=14.1 Hz, 4a-C), 145.2 (quat, 8-C), 147.3 (quat, 5a-C), 169.5 (quat, td, J=20.0, 4.9 Hz, 3-C); δF (282 MHz, DMSO-d6) -279.65 (1F, s, 4-F), -268.13 (1F, d, J=11.3 Hz, 2-F), -264.22 (1F, d, J=11.8 Hz, 1-F).

Reference： [1]Bedernjak, Alexandre F.; Groundwater, Paul W.; Gray, Mark; James, Arthur L.; Orenga, Sylvain; Perry, John D.; Anderson, Rosaleen J. [Tetrahedron, 2013, vol. 69, # 39, p. 8456 - 8462]

18
[ 527-21-9 ]
[ 603-85-0 ]
[ 1451044-42-0 ]

Yield	Reaction Conditions	Operation in experiment
15%	With sodium acetate In ethanol	7 4.2.7 9-Nitro-1,2,4-trifluoro-3H-phenoxazin-3-one (7a) 4.2.7 9-Nitro-1,2,4-trifluoro-3H-phenoxazin-3-one (7a) The title compound was prepared from p-fluoranil 11c (0.90 g, 5.00 mmol) and 2-amino-3-nitrophenol 10 (0.74 g, 4.82 mmol) according to the general procedure. The precipitate was taken into EtOAc (100 mL) and the resulting mixture filtered through a sintered funnel. The insoluble residue was washed several time with EtOAc and discarded. The combined organic filtrates were washed with water (1100 mL), brine (1100 mL) and dried (MgSO4). The solvent was removed under reduced pressure and the residue subjected to column chromatography, eluting with petroleum ether 60-80 °C/EtOAc (80:20). Compound 7a was isolated as a dark red solid (0.22 g, 0.73 mmol, 15%). Ruby red prisms of 7a with a metallic lustre were obtained from glacial acetic acid, mp: 216-218 °C; (found: C, 48.5; H, 1.0; N, 9.2%. C12H3F3N2O4 requires C, 48.7; H, 1.0; N, 9.5%); (found: (MH)+, 297.0118. Calcd for C12H4F3N2O4: (MH)+, 297.0118); νmax/cm-1 3084 (C-H), 1649 (C=O), 1603 (C=C), 1530 and 1313 (NO2), 1004 (C-F); δH (300 MHz, THF-d8) 6.04-6.13 (m, 3H, 6-H, 7-H and 8-H); δC (75 MHz, THF-d8) 117.6 (CH, 8-C), 117.9 (CH, 6-C), 123.0 (quat, 9a-C), 130.0 (quat, ddd, J=10.0, 5.0, 1.2 Hz, 10a-C), 131.5 (CH, 7-C), 135.8 (quat, dd, J=261.9, 6.3 Hz, 4-C), 140.7 (quat, ddd, J=18.2, 4.8, 1.2 Hz, 4a-C), 141.4 (quat, dt, J=273.2, 6.8 Hz, 2-C), 141.5 (quat, d, J=1.7 Hz, 5a-C), 142.1 (quat, dd, J=274.7, 12.2 Hz, 1-C), 146.4 (quat, 9-C), 166.7 (quat, td, J=21.1, 5.5 Hz, 3-C); δF (282 MHz, THF-d8) -282.53 (1F, t, J=2.3 Hz, 4-F), -271.43 (1F, dd, J=9.0, 2.3 Hz, 1-F), -265.36 (1F, dd, J=9.3, 2.3 Hz, 2-F); δH (300 MHz, DMSO-d6) 7.95 (1H, t, J=8.4 Hz, 7-H), 8.01 (1H, dd, J=8.4, 1.8 Hz, 8-H), 8.08 (1H, dd, J=7.5, 1.8 Hz, 6-H); δC (75 MHz, DMSO-d6) 120.5 (CH, 8-C), 120.7 (CH, 6-C), 124.8 (quat, 9a-C), 132.8 (quat, dd, J=9.0, 4.5 Hz, 10a-C), 134.6 (CH, 7-C), 137.5 (quat, dd, J=255.0, 6.0 Hz, 4-C), 142.7 (quat, ddd, J=17.3, 4.5, 1.5 Hz, 4a-C), 143.2 (quat, d, J=0.8 Hz, 5a-C), 143.3 (quat, dt, J=267.8, 7.5 Hz, 2-C), 144.0 (quat, dd, J=270.0, 10.5 Hz, 1-C), 147.8 (quat, 9-C), 169.4 (quat, td, 21.0, 6.0 Hz, 3-C); δF (282 MHz, DMSO-d6) -280.98 (1F, t, J=2.3 Hz, 4-F), -268.59 (1F, dd, J=11.0, 2.3 Hz, 1-F), -262.77 (1F, dd, J=11.0, 2.3 Hz, 2-F).

Reference： [1]Bedernjak, Alexandre F.; Groundwater, Paul W.; Gray, Mark; James, Arthur L.; Orenga, Sylvain; Perry, John D.; Anderson, Rosaleen J. [Tetrahedron, 2013, vol. 69, # 39, p. 8456 - 8462]

19
[ 527-21-9 ]
[ 121-88-0 ]
[ 1451044-44-2 ]
[ 1451044-40-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 12%	With sodium acetate In ethanol for 24h;	2 7-Nitro-1,2,4-trifluoro-3H-phenoxazin-3-one (5a) and 3,10-dinitro-6,13-difluorotriphenodioxazine (12a) The title compounds were prepared from p-fluoranil 11a (1.90g, 10.57mmol) and 2-amino-5-nitrophenol 8 (1.42g, 9.61mmol) according to the general procedure. Water (100mL) was added to the reaction mixture and the resulting mixture was extracted with EtOAc (3×60mL). The emulsion was filtered through a sintered funnel and the insoluble residue was washed several times with EtOAc, giving 12a as a dark violet solid (1.91g, 4.63mmol, 48%). A dark violet microcrystalline solid was obtained from nitrobenzene, mp: 315°C (dec); (found: (MH)+, 413.0324. Calcd for C18H7F2N4O6: (MH)+, 413.0328); νmax/cm-1 3104 (C-H), 1622 (C=N), 1595 and 1579 (C=C), 1515 and 1332 (NO2). The aqueous layer was discarded and the combined EtOAc filtrates and layers were washed with water (150mL) and brine (150mL), and dried (MgSO4). The solvent was removed in vacuo and the residue subjected to column chromatography on silica, eluting with petroleum ether 60-80°C/EtOAc (80:20). Nitrophenoxazinone 5a was isolated as a dark purple solid (0.35g, 1.19mmol, 12%). Dark red-purple needle-like crystals were obtained from glacial acetic acid, mp: 218-220°C; (found: C, 48.5; H, 1.05; N, 9.15%. C12H3F3N2O4 requires C, 48.7; H, 1.0; N, 9.5%); (found: (MH)+, 297.0118. Calcd for C12H4F3N2O4: (MH)+, 297.0118); νmax/cm-1 3104 (C-H), 1660 (C=O), 1596 (C=C), 1531 and 1312 (NO2), 1003 (C-F); δH (300MHz, THF-d8) 6.41 (1H, d, J=8.7Hz, 9-H), 6.58 (1H, dd, J=8.7, 2.4Hz, 8-H), 6.74 (1H, d, J=2.4Hz, 6-H); δC (75MHz, THF-d8) 110.3 (CH, 6-C), 118.6 (CH, 8-C), 129.4 (CH, 9-C), 130.1 (quat, ddd, J=8.5, 5.2, 1.4Hz, 10a-C), 134.1 (quat, 9a-C), 136.0 (quat, dd, J=262.7, 6.1Hz, 4-C), 141.3 (quat, dt, J=273.4, 6.9Hz, 2-C), 142.2 (quat, dd, J=273.4, 12.2Hz, 1-C), 141.4 (quat, d, J=1.5Hz, 5a-C), 141.7 (quat, ddd, J=18.1, 4.8, 1.2Hz, 4a-C), 147.9 (quat, 7-C), 166.7 (quat, td, J=21.4, 5.4Hz, 3-C); δF (282MHz, THF-d8) -282.17 (1F, t, J=2.3Hz, 4-F), -271.89 (1F, dd, J=9.3, 2.0Hz, 2-F), -265.41 (1F, dd, J=9.3, 2.0Hz, 1-F); δH (300MHz, DMSO-d6) 8.23 (1H, d, J=8.7Hz, 9-H), 8.31 (1H, dd, J=8.7, 2.4Hz, 8-H), 8.54 (1H, d, J=2.4Hz, 6-H); δC (75MHz, DMSO-d6) 112.3 (CH, 6-C), 120.8 (CH, 8-C), 131.4 (CH, 9-C), 132.1 (quat, dd, J=9.4, 3.0Hz, 10a-C), 135.4 (quat, 9a-C), 136.0 (quat, dd, J=262.7, 6.1Hz, 4-C), 142.6 (quat, dt, J=268.2, 6.1Hz, 2-C), 143.6 (quat, dd, J=270.4, 11.7Hz, 1-C), 142.5 (quat, 5a-C), 141.7 (quat, ddd, J=18.1, 4.8, 1.2Hz, 4a-C), 149.1 (quat, 7-C), 168.9 (quat, td, J=20.3, 5.6Hz, 3-C); δF (282MHz, DMSO-d6) -280.43 (1F, s, 4-F), -268.27 (1F, d, J=11.9Hz, 2-F), -263.04 (1F, d, J=11.3Hz, 1-F).

Reference： [1]Bedernjak, Alexandre F.; Groundwater, Paul W.; Gray, Mark; James, Arthur L.; Orenga, Sylvain; Perry, John D.; Anderson, Rosaleen J. [Tetrahedron, 2013, vol. 69, # 39, p. 8456 - 8462]

20
[ 392-56-3 ]
difluoromaleic acid [ No CAS ]
[ 527-21-9 ]
[ 771-63-1 ]
[ 771-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In acetonitrile at 60℃; for 15h;

Reference： [1]Colomban, Cédric; Kudrik, Evgenij V.; Afanasiev, Pavel; Sorokin, Alexander B. [Journal of the American Chemical Society, 2014, vol. 136, # 32, p. 11321 - 11330]

21
[ 527-21-9 ]
[ 115859-76-2 ]
6,7,9-trifluoro-5a-hydroxy-10-(4-methylbenzoyl)-1,2,3,4-tetrahydropyrimido[1,2-a]indol-8(5aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

22
[ 527-21-9 ]
[ 82100-30-9 ]
10-benzoyl-6,7,9-trifluoro-5a-hydroxy-1,2,3,4-tetrahydro-pyrimido[1,2-a]indol-8(5aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

23
[ 527-21-9 ]
[ 107165-83-3 ]
10-(4-chlorobenzoyl)-6,7,9-trifluoro-5a-hydroxy-1,2,3,4-tetra-hydropyrimido[1,2-a]indol-8(5aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

24
[ 527-21-9 ]
[ 124927-45-3 ]
7,8,10-trifluoro-6a-hydroxy-11-(4-methoxybenzoyl)-2,3,4, 5-tetrahydro-1H-[1,3]diazepino[1,2-a]indol-9(6aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

25
[ 527-21-9 ]
[ 115859-69-3 ]
7,8,10-trifluoro-6a-hydroxy-11-(4-methylbenzoyl)-2,3,4, 5-tetrahydro-1H-[1,3]diazepino[1,2-a]indol-9(6aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

26
[ 527-21-9 ]
[ 115859-77-3 ]
11-benzoyl-7,8,10-trifluoro-6a-hydroxy-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]indol-9(6aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

27
[ 527-21-9 ]
[ 124927-46-4 ]
11-(4-chlorobenzoyl)-7,8,10-trifluoro-6a-hydroxy-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]indol-9(6aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In acetone at 20℃; for 0.333333h; Green chemistry;	General Procedure for the Preparation of Fused Polyhalogeno-7a-hydroxy-[1,2-a]indol-5-ones 3 General procedure: HKA derivatives 1 (0.5 mmol) was added to a 25 mL round-bottomed flask and dissolved in Acetone (5ml), an acetone solution (10 ml) of halogenated quinone derivatives 2 (0.5 mmol) was charged into a 25 ml dropping funnel and added slowly and dropwise over a period of 10 minutes. After all the acetone solution was added, monitored by TLC, and also the mixture was stirred at room temperature for 10 minutes. When the reaction completed as indicated by TLC, filtered to give the pure crude product, which was further washed by 95 % EtOH to give pure product 3 with a yield of 71-97 %. The products were further identified by FTIR, NMR and HRMS, being in good agreement with the assigned structures. (See Supplementary Information).

Reference： [1]Yu, Fu-Chao; Hao, Xiao-Pan; Lin, Xin-Rong; Yan, Sheng-Jiao; Lin, Jun [Tetrahedron, 2015, vol. 71, # 24, p. 4084 - 4089]

28
[ 527-21-9 ]
[ 62-53-3 ]
[ 603-35-0 ]
[ 139-59-3 ]
6-(4-phenoxyphenylamino)-5-fluoro-4-oxo-3-(phenylimino)-2-(triphenylphosphonio)cyclohexa-1,5-dien-1-olate [ No CAS ]
4-(4-phenoxyanilino)-5-fluoro-3,6-dioxo-2-(triphenylphosphonio)cyclohexa-1,4-dien-1-olate [ No CAS ]
[ 791-28-6 ]