- Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN
-
A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.
- Yao, Yunxin,Zhao, Guangkuan,Hamze, Abdallah,Alami, Mouad,Provot, Olivier
-
p. 5775 - 5779
(2020/08/17)
-
- SBA-15 functionalized sulfonic acid containing a confined hydrophobic and acidic ionic liquid: A highly efficient catalyst for solvent-free thioacetalization of carbonyl compounds at room temperature
-
A novel application of SBA-15 functionalized sulfonic acid containing a confined ionic liquid has been introduced to convert various carbonyl compounds to their corresponding dithioacetals and dithioketals at room temperature and under solvent-free condit
- Karimi, Babak,Vafaeezadeh, Majid
-
p. 23207 - 23211
(2013/11/19)
-
- Facile deprotection of dithioacetals by using a novel 1,4-benzoquinone/cat. NaI system
-
The combination of 1,4-benzoquinone and a catalytic amount of NaI was found to be effective for the deprotection of dithioacetals. The reactions proceeded efficiently under mild, near-neutral reaction conditions, producing a wide range of aryl and alkyl aldehydes and ketones generally in high yields with good functional group compatibility. The method developed therefore represents a general, facile, and highly applicable approach for deprotecting dithioacetals.
- Inamoto, Kiyofumi,Yamada, Tetsuya,Kato, Sei-Ichi,Kikkawa, Shoko,Kondo, Yoshinori
-
p. 9192 - 9199
(2013/10/01)
-
- Silica-supported phosphorus pentoxide: A reusable catalyst for S,S-acetalization of carbonyl groups under ambient conditions
-
Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) efficiently acts as a highly active and reusable catalyst for cyclic and non-cyclic S,S-acetalization of a variety of carbonyl compounds under mild, solvent-free an
- Shaterian, Hamid Reza,Azizi, Kobra,Fahimi, Nafiseh
-
experimental part
p. 85 - 91
(2012/01/06)
-
- Chemoselective (trans)thioacetalization of carbonyl compounds with a reusable lewis acid-surfactant-combined copper bis(dodecyl sulfate) catalyst in water
-
A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS) 2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields. Georg Thieme Verlag Stuttgart.
- Weng, Shiue-Shien,Chang, Shen-Chun,Chang, Tsuan-Hao,Chyn, Jong-Pyng,Lee, Shu-Wei,Lin, Chao-An,Chen, Fong-Kuang
-
experimental part
p. 1493 - 1499
(2010/10/03)
-
- Catalytic carbon-sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
-
A series of thiols have been examined as protic nucleophiles for Michael-type additions to α,β-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner.
- Chen, Chien-Tien,Lin, Yow-Dzer,Liu, Cheng-Yuan
-
supporting information; experimental part
p. 10470 - 10476
(2010/02/28)
-
- Oxalic acid-promoted preparation of dithioacetals from carbonyl compounds or acetals
-
This letter describes oxalic acid-promoted syntheses of dithioacetals from carbonyl compounds and thiols. Acetals are also converted into dithioacetals by the reaction with thiols under similar conditions. Copyright
- Miyake, Hideyoshi,Nakao, Yuichi,Sasaki, Mitsuru
-
p. 104 - 105
(2007/10/03)
-
- Bismuth oxide perchlorate as a highly efficient and chemoselective catalyst for thioacetalization of carbonyl compounds under solvent-free conditions
-
Bismuth oxide perchlorate efficiently and chemoselectively catalyzes the thioacetalization of both aliphatic and aromatic carbonyl compounds under solvent-free conditions. Stearically hindered ketones are also thioacetalized in excellent yields with stoic
- Sunil Kumar,Thirupathi Reddy,Narsimha Reddy,Rao,Rajitha
-
p. 2387 - 2389
(2007/10/03)
-
- Highly efficient and chemoselective thioacetalization of carbonyl compounds catalyzed with aluminum trifluromethanesulfonate [Al(OTf)3]
-
Aluminum trifluromethanesulfonate [Al(OTf)3] is a highly efficient and chemoselective catalyst for the thioacetalization of carbonyl compounds.
- Firouzabadi,Iranpoor,Kohmareh
-
p. 167 - 173
(2007/10/03)
-
- Trichloroisocyanuric acid as a mild and efficient catalyst for thioacetalization and transthio-acetalization reactions
-
Trichloroisocyanuric acid (1), a cheap industrial chemical, catalyzes mild and efficient thioacetalization and transthioacetalization reactions. In addition, this catalyst is very selective for this purpose.
- Firouzabadi,Iranpoor,Hazarkhani
-
p. 1641 - 1643
(2007/10/03)
-
- Molybdenum pentachloride (MoCl5) catalyzes efficient dithioacetalization of carbonyl compounds and transdithioacetalization of O, O-acetals. This catalyst also conducts efficient non-hydrolytic deprotection of dithioacetals in the presence of dry DMSO. Part 2
-
Dithioacetalization of carbonyl compounds was performed efficiently in CH2Cl2 at room temperature in the presence of MoCl5. Highly selective transdithioacetalization of acetals was also catalyzed efficiently by this catalyst. MoCl5 performed non-hydrolytic deprotection of dithioacetals in the presence of dry DMSO.
- Firouzabadi,Karimi
-
p. 207 - 216
(2007/10/03)
-
- Neutral lithium triflate (LiOTf) efficiently catalyzes chemoselective preparations of cyclic and acyclic dithioacetals from carbonyl compounds, acylals, and O,O-cyclic and open-chain acetals under solvent-free conditions
-
An efficient and chemoselective preparation of cyclic and acyclic thioacetals from carbonyl compounds, cyclic and acyclic acetals and acylals in the presence of catalytic amounts of neutral lithium triflate and thiols under solvent-free conditions is described.
- Firouzabadi, Habib,Eslami, Shahram,Karimi, Babak
-
p. 2401 - 2406
(2007/10/03)
-
- Highly efficient transdithioacetalization of acetals catalyzed by silica chloride
-
A modified procedure for the preparation of a silica chloride with higher chloride capacity than that reported is described. Moreover, this silica chloride was found to be an effective catalyst for chemoselective and highly efficient transdithioacetalization of different classes of acetals.
- Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak,Hazarkhani, Hassan
-
p. 263 - 265
(2007/10/03)
-
- Zirconium tetrachloride (ZrCl4) catalyzed highly chemoselective and efficient transthioacetalization of acetals
-
Zirconium tetrachloride (ZrCl4) is an efficient catalyst for the highly chemoselective transthioacetalization of acetals under mild reaction conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Karimi, Babak
-
p. 319 - 320
(2007/10/03)
-
- Lithium trifluoromethanesulfonate (LiOTf) as a highly efficient catalyst for chemoselective dithioacetalization of carbonyl compounds under neutral and solvent-free conditions
-
Various types of carbonyl compound can be efficiently and chemoselectively converted to their corresponding dithioacetals in the presence of catalytic amounts of lithium triflate under solvent-free conditions. Due to the neutrality of the reaction medium, this method is especially useful for acid sensitive substrates.
- Firouzabadi, Habib,Karimi, Babak,Eslami, Shahram
-
p. 4055 - 4058
(2007/10/03)
-
- Pyrylium Salt Sensitized Photochemical Deprotections of Dithioacetals and Ketals
-
Photoreactions of various dithioacetals and ketals using tris(p-chlorophenyl)pyrylium perchlorate as a sensitizer were studied.Irradiation (λ>360 nm) of dichloromethane solutions containing dithioacetals or ketals and pyrylium salt afforded the corresponding carbonyl compounds in good to excellent yields in the presence of molecular oxygen.
- Kamata, Masaki,Murakami, Yukiko,Tamagawa, Yasuko,Kato, Mitsuaki,Hasegawa, Eietsu
-
p. 12821 - 12828
(2007/10/02)
-