1-(4-'AlkylH'phenyl)-2-Alkylethan-1-one to 1-(4-'AlkylH'phenyl)-2-Alkyl-2-iodoethan-1-one [Re

Query Query O ALK

ALK

1. Query I ALH

Results

Date

16 reactions in Reaxys

2016-03-09 09h:43m:43s (EST)

O

ALH

Search as: As drawn, No salts, No mixtures

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

1/8

2016-03-09 09:48:24

O

O I

Rx-ID: 9264549 View in Reaxys 1/16 Yield 90 %

Conditions & References With iodine in ethylene glycol dimethyl ether, Time= 3h, T= 90 °C Rao, Maddali L.N.; Jadhav, Deepak N.; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6883 - 6886 View in Reaxys

86 %

With (hydroxy(tosyloxy)iodo)benzene, iodine, 1-n-butyl-3-methylimidazolium tetrafluoroborate, T= 60 °C , Ionic liquid Lee, Jong Chan; Kim, Jimi; Park, Hyun Jung; Kwag, Byungmook; Lee, Seung Bae; Bulletin of the Korean Chemical Society; vol. 31; nb. 5; (2010); p. 1385 - 1386 View in Reaxys

85 %

Stage 1: With (hydroxy(tosyloxy)iodo)benzene, Time= 0.025h, microwave irradiation Stage 2: With magnesium iodide, Time= 0.0333333h, microwave irradiation, Further stages.

Lee, Jong Chan; Park, Jin Young; Yoon, So Young; Bae, Yong Hun; Lee, Seung Jun; Tetrahedron Letters; vol.

45; nb. 1; (2004); p. 191 - 193 View in Reaxys

85 %

4 : 4.2.2. The reaction of propiophenone 1a with I2O5.

In a sealed tube(25 mL), propiophenone 1a (0.25 mmol), I2O5 (0.25 mmol), andCH3CN (2 mL) were added. The reaction vessel was allowed to stir at80 C for 48 h. After the reaction, the solution was concentrated invacuum. The resulting mixture purified by flash column chromatographyusing amixture of petroleumether and ethyl acetate as eluentto give the desired 2-iodo-1-phenylpropan-1-one 4a in 85percent yield.

With di-iodine pentaoxide in acetonitrile, Time= 48h, T= 80 °C Liu, Chunli; Wei, Wei; Yang, Daoshan; Zheng, Yuanyuan; Bi, Yanshuai; Chen, Min; Wang, Hua; Tetrahedron; vol. 71; nb. 38; (2015); p. 6901 - 6906 View in Reaxys

78 %

With N-iodo-succinimide, toluene-4-sulfonic acid, Microwave irradiation Lee, Jong Chan; Bae, Yong Hun; Synlett; nb. 4; (2003); p. 507 - 508 View in Reaxys

35 %

General procedure for the iodination of carbonyl compounds: General procedure: Oxone.(R). (2.2 mmol) was slowly added to a well stirred solution of NH4I (2.2 mmol) and carbonyl compound (2 mmol) in methanol and the reaction mixture was allowed to stir at room or reflux temperature. After disappearance of the reactant (reaction was monitored by TLC) or after the appropriate time, the reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, insoluble material filtered off, the solution washed with aqueous sodium thiosulfate pentahydrate (5percent) and water. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude reaction mixture was further purified by column chromatography using silica gel (230-400 mesh) gave the target products. All the products were identified by their 1H NMR, 13C NMR and mass spectra.

With NH4I, Oxonereg; in methanol, Time= 48h, T= 20 °C Marri, Mahender Reddy; MacHarla, Arun Kumar; Peraka, Swamy; Nama, Narender; Tetrahedron Letters; vol. 52; nb. 49; (2011); p. 6554 - 6559 View in Reaxys

11 %

With copper(l) iodide, oxygen, acetic acid in dimethyl sulfoxide, T= 120 °C Du, Juan; Zhang, Xiuli; Sun, Xi; Wang, Lei; Chemical Communications; vol. 51; nb. 21; (2015); p. 4372 - 4375 View in Reaxys Reaction Steps: 2 1: H2SO4, Cu(OAc)2 2: I2, TlOAc / acetic acid

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/8

2016-03-09 09:48:24

With copper diacetate, sulfuric acid, iodine, thallous acetate in acetic acid Cambie,R.C. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 126 - 130 View in Reaxys 38 %Spectr.

With iodine, benzoic acid in ethyl acetate, Time= 36h, T= 75 °C Uyanik, Muhammet; Suzuki, Daisuke; Yasui, Takeshi; Ishihara, Kazuaki; Angewandte Chemie - International Edition; vol. 50; nb. 23; (2011); p. 5331 - 5334 View in Reaxys With N-iodo-succinimide, toluene-4-sulfonic acid, Time= 1h, Milling Estevez, Veronica; Villacampa, Mercedes; Menendez, J. Carlos; Chemical Communications; vol. 49; nb. 6; (2013); p. 591 - 593 View in Reaxys Reaction Steps: 2 1: bromine 2: 2,6-di-tert-butyl-4-methyl-phenol; potassium iodide; caesium carbonate / toluene / 24 h / 100 °C / |Inert atmosphere With 2,6-di-tert-butyl-4-methyl-phenol, bromine, caesium carbonate, potassium iodide in toluene Xu, Tao; Hu, Xile; Angewandte Chemie - International Edition; vol. 54; nb. 4; (2015); p. 1307 - 1311; Angew. Chem.; vol. 127; nb. 4; (2015); p. 1323 - 1327,5 View in Reaxys

O

O

I

Rx-ID: 2956948 View in Reaxys 2/16 Yield

Conditions & References

96 %

With (hydroxy(tosyloxy)iodo)benzene, iodine, 1-n-butyl-3-methylimidazolium tetrafluoroborate, T= 60 °C , Ionic liquid Lee, Jong Chan; Kim, Jimi; Park, Hyun Jung; Kwag, Byungmook; Lee, Seung Bae; Bulletin of the Korean Chemical Society; vol. 31; nb. 5; (2010); p. 1385 - 1386 View in Reaxys

89 %

With iodine, mercury dichloride in dichloromethane, Time= 1h, Ambient temperature Barluenga, Jose; Martinez-Gallo, Jose M.; Najera, Carmen; Yus, Miguel; Synthesis; nb. 8; (1986); p. 678 - 680 View in Reaxys

86 %

With iodine in ethylene glycol dimethyl ether, Time= 3h, T= 90 °C Rao, Maddali L.N.; Jadhav, Deepak N.; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6883 - 6886 View in Reaxys

80 %

Stage 1: With (hydroxy(tosyloxy)iodo)benzene, Time= 0.025h, microwave irradiation Stage 2: With magnesium iodide, Time= 0.0333333h, microwave irradiation, Further stages.

Lee, Jong Chan; Park, Jin Young; Yoon, So Young; Bae, Yong Hun; Lee, Seung Jun; Tetrahedron Letters; vol.

45; nb. 1; (2004); p. 191 - 193 View in Reaxys O

O

O

I

Cl

Rx-ID: 40520123 View in Reaxys 3/16

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/8

2016-03-09 09:48:24

Yield

Conditions & References

9 General procedure for vanadium-catalyzed iodination under atmospheric molecular oxygen %Spectr., General procedure: In a 5 mL three-necked flask, Bu4NI (111 mg, 0.3 mmol), AlI3(122 mg, 0.3 mmol), and NH4VO3 7 %Spectr. (2.9 mg, 0.025 mmol) were placed.The flask was evacuated and backfilled with molecular oxygen. To the mixture, acetonitrile (1 mL) and a substrate (0.25 mmol) were added. The mixture was stirred at 80 °C under atmospheric molecular oxygen,followed by treatment with 1:1 mixture of saturated Na2S2O3 aqueous solution and saturated NaHCO3 aqueous solution, and extraction with ether. The organic layer was dried over MgSO4, filtered, and evaporated.

1,2,4,5-Tetramethylbenzene was added as an internal standard, and 1H NMR analysis was performed to determine an NMR yield. Spectral data of the products were identical with those of commercially available and authentic samples With AlCl3, aluminium chloride, ammonium metavanadate, oxygen, potassium iodide in acetonitrile, Time= 24h, T= 80 °C Moriuchi, Toshiyuki; Fukui, Yasuhiro; Kato, Satoshi; Kajikawa, Tomomi; Hirao, Toshikazu; Journal of Inorganic Biochemistry; vol. 147; (2015); p. 177 - 180 View in Reaxys 58 %Spectr., 16 %Spectr.

General procedure for vanadium-catalyzed iodination under atmospheric molecular oxygen General procedure: In a 5 mL three-necked flask, Bu4NI (111 mg, 0.3 mmol), AlI3(122 mg, 0.3 mmol), and NH4VO3 (2.9 mg, 0.025 mmol) were placed.The flask was evacuated and backfilled with molecular oxygen. To the mixture, acetonitrile (1 mL) and a substrate (0.25 mmol) were added. The mixture was stirred at 80 °C under atmospheric molecular oxygen,followed by treatment with 1:1 mixture of saturated Na2S2O3 aqueous solution and saturated NaHCO3 aqueous solution, and extraction with ether. The organic layer was dried over MgSO4, filtered, and evaporated.

1,2,4,5-Tetramethylbenzene was added as an internal standard, and 1H NMR analysis was performed to determine an NMR yield. Spectral data of the products were identical with those of commercially available and authentic samples With aluminium(III) iodide, ammonium metavanadate, tetrabutyl-ammonium chloride, oxygen in acetonitrile, Time= 24h, T= 80 °C , Reagent/catalyst Moriuchi, Toshiyuki; Fukui, Yasuhiro; Kato, Satoshi; Kajikawa, Tomomi; Hirao, Toshikazu; Journal of Inorganic Biochemistry; vol. 147; (2015); p. 177 - 180 View in Reaxys O

O

I

O HO

Rx-ID: 40520124 View in Reaxys 4/16 Yield 49 %Spectr.

Conditions & References General procedure for vanadium-catalyzed iodination under atmospheric molecular oxygen General procedure: In a 5 mL three-necked flask, Bu4NI (111 mg, 0.3 mmol), AlI3(122 mg, 0.3 mmol), and NH4VO3 (2.9 mg, 0.025 mmol) were placed.The flask was evacuated and backfilled with molecular oxygen. To the mixture, acetonitrile (1 mL) and a substrate (0.25 mmol) were added. The mixture was stirred at 80 °C under atmospheric molecular oxygen,followed by treatment with 1:1 mixture of saturated Na2S2O3 aqueous solution and saturated NaHCO3 aqueous solution, and extraction with ether. The organic layer was dried over MgSO4, filtered, and evaporated.

1,2,4,5-Tetramethylbenzene was added as an internal standard, and 1H NMR analysis was performed to determine an NMR yield. Spectral data of the products were identical with those of commercially available and authentic samples With AlCl3, aluminium chloride, ammonium metavanadate, oxygen, potassium iodide in acetonitrile, Time= 48h, T= 80 °C , Time Moriuchi, Toshiyuki; Fukui, Yasuhiro; Kato, Satoshi; Kajikawa, Tomomi; Hirao, Toshikazu; Journal of Inorganic Biochemistry; vol. 147; (2015); p. 177 - 180 View in Reaxys O

O

O

I

O

HO

Rx-ID: 32091543 View in Reaxys 5/16

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/8

2016-03-09 09:48:24

Yield

Conditions & References

90 %, 8 %

General procedure for the iodination of carbonyl compounds: General procedure: Oxone.(R). (2.2 mmol) was slowly added to a well stirred solution of NH4I (2.2 mmol) and carbonyl compound (2 mmol) in methanol and the reaction mixture was allowed to stir at room or reflux temperature. After disappearance of the reactant (reaction was monitored by TLC) or after the appropriate time, the reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, insoluble material filtered off, the solution washed with aqueous sodium thiosulfate pentahydrate (5percent) and water. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude reaction mixture was further purified by column chromatography using silica gel (230-400 mesh) gave the target products. All the products were identified by their 1H NMR, 13C NMR and mass spectra.

With NH4I, Oxonereg;, Time= 10h, Reflux Marri, Mahender Reddy; MacHarla, Arun Kumar; Peraka, Swamy; Nama, Narender; Tetrahedron Letters; vol. 52; nb. 49; (2011); p. 6554 - 6559 View in Reaxys

O

O

I

Rx-ID: 10289921 View in Reaxys 6/16 Yield

Conditions & References

87 %

With iodine in ethylene glycol dimethyl ether, Time= 3h, T= 90 °C Rao, Maddali L.N.; Jadhav, Deepak N.; Tetrahedron Letters; vol. 47; nb. 38; (2006); p. 6883 - 6886 View in Reaxys O

O

I

O O

Rx-ID: 3399322 View in Reaxys 7/16 Yield

Conditions & References

66 %, 24 % With iodine, trimethyl orthoformate, Time= 24h, T= 23 °C Yamauchi, Takayoshi; Hattori, Kaneaki; Nakao, Kenji; Tamaki, Kentaro; Journal of Organic Chemistry; vol. 53; nb. 20; (1988); p. 4858 - 4859 View in Reaxys O

O

I

Rx-ID: 9248167 View in Reaxys 8/16 Yield 90 %

Conditions & References With N-iodo-succinimide, toluene-4-sulfonic acid, Microwave irradiation Lee, Jong Chan; Bae, Yong Hun; Synlett; nb. 4; (2003); p. 507 - 508 View in Reaxys

84 %

With (hydroxy(tosyloxy)iodo)benzene, iodine, 1-n-butyl-3-methylimidazolium tetrafluoroborate, T= 60 °C , Ionic liquid Lee, Jong Chan; Kim, Jimi; Park, Hyun Jung; Kwag, Byungmook; Lee, Seung Bae; Bulletin of the Korean Chemical Society; vol. 31; nb. 5; (2010); p. 1385 - 1386 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/8

2016-03-09 09:48:24

O

O O

O

I

O

O

O

Rx-ID: 3399310 View in Reaxys 9/16 Yield

Conditions & References

24 %, 66 % With iodine, Time= 24h, T= 23 °C Yamauchi, Takayoshi; Hattori, Kaneaki; Nakao, Kenji; Tamaki, Kentaro; Journal of Organic Chemistry; vol. 53; nb. 20; (1988); p. 4858 - 4859 View in Reaxys O

O

O O

O I

O O

O I

O

Rx-ID: 3919309 View in Reaxys 10/16 Yield

Conditions & References

23 %, 2 %, With iodine, Time= 24h, T= 23 °C 69 % Yamauchi, Takayoshi; Hattori, Kaneaki; Nakao, Kenji; Tamaki, Kentaro; Journal of Organic Chemistry; vol. 53; nb. 20; (1988); p. 4858 - 4859 View in Reaxys

O

O

O

O

I O

HO

O

Rx-ID: 31038860 View in Reaxys 11/16 Yield 17 %Spectr., 13 %Spectr.

Conditions & References With tetra(n-butyl)ammonium hydroxide, iodine in ethyl acetate, Time= 36h, T= 75 °C Uyanik, Muhammet; Suzuki, Daisuke; Yasui, Takeshi; Ishihara, Kazuaki; Angewandte Chemie - International Edition; vol. 50; nb. 23; (2011); p. 5331 - 5334 View in Reaxys

O

O H N

O

I

N

O O

Rx-ID: 39021591 View in Reaxys 12/16 Yield 97 %Chromat., 5.2 mg

Conditions & References With Na2CO3*1.5H2O2, NH4I in acetonitrile, Time= 18h, T= 50 °C Jiang, Qing; Xu, Bin; Zhao, An; Jia, Jing; Liu, Tian; Guo, Cancheng; Journal of Organic Chemistry; vol. 79; nb.

18; (2014); p. 8750 - 8756 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/8

2016-03-09 09:48:24

O

O

I

bis<chloro(η3-1,3-diphenylallyl)palladium> Rx-ID: 16269965 View in Reaxys 13/16 Yield

Conditions & References Reaction Steps: 2 1: acetonitrile / Heating 2: potassium iodide; 18-crown-6 / acetonitrile / 1 h / 20 °C With 18-crown-6 ether, potassium iodide in acetonitrile, 1: sulfonyloxylation / 2: Iodination Lee, Jong Chan; Jin, Yong Suk; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2769 - 2774 View in Reaxys Reaction Steps: 2 1: acetonitrile / Heating 2: potassium iodide; 18-crown-6 / acetonitrile / 1 h / 20 °C With 18-crown-6 ether, potassium iodide in acetonitrile, 1: sulfonyloxylation / 2: Iodination Lee, Jong Chan; Jin, Yong Suk; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2769 - 2774 View in Reaxys O

O

2-methyl-5-propyl-phenyl magnesium bro‐ mide

I

Rx-ID: 16259636 View in Reaxys 14/16 Yield

Conditions & References Reaction Steps: 2 1: acetonitrile / Heating 2: potassium iodide; 18-crown-6 / acetonitrile / 1 h / 20 °C With 18-crown-6 ether, potassium iodide in acetonitrile, 1: sulfonyloxylation / 2: Iodination Lee, Jong Chan; Jin, Yong Suk; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2769 - 2774 View in Reaxys

O

O I

O

O

Rx-ID: 39423711 View in Reaxys 15/16 Yield

Conditions & References Reaction Steps: 2 1: bromine 2: 2,6-di-tert-butyl-4-methyl-phenol; copper(II) bis(trifluoromethanesulfonate); 2,6-bis[(4S)-isopropyl-2-oxazolin-2yl]pyridine; potassium iodide; caesium carbonate / toluene / 24 h / 100 °C / |Inert atmosphere With 2,6-di-tert-butyl-4-methyl-phenol, bromine, copper(II) bis(trifluoromethanesulfonate), caesium carbonate, 2,6bis[(4S)-isopropyl-2-oxazolin-2-yl]pyridine, potassium iodide in toluene Xu, Tao; Hu, Xile; Angewandte Chemie - International Edition; vol. 54; nb. 4; (2015); p. 1307 - 1311; Angew. Chem.; vol. 127; nb. 4; (2015); p. 1323 - 1327,5 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

7/8

2016-03-09 09:48:24

O

O I

O

Rx-ID: 39423714 View in Reaxys 16/16 Yield

Conditions & References Reaction Steps: 2 1: bromine 2: 1,1-di(phenyl)ethylene; copper(II) bis(trifluoromethanesulfonate); 2,6-bis[(4S)-isopropyl-2-oxazolin-2-yl]pyridine; potassium iodide; caesium carbonate / toluene / 24 h / 100 °C / |Inert atmosphere With 1,1-di(phenyl)ethylene, bromine, copper(II) bis(trifluoromethanesulfonate), caesium carbonate, 2,6-bis[(4S)-isopropyl-2-oxazolin-2-yl]pyridine, potassium iodide in toluene Xu, Tao; Hu, Xile; Angewandte Chemie - International Edition; vol. 54; nb. 4; (2015); p. 1307 - 1311; Angew. Chem.; vol. 127; nb. 4; (2015); p. 1323 - 1327,5 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/8

2016-03-09 09:48:24