7695-69-4Relevant academic research and scientific papers
Direct Synthesis of Unsymmetrical Dithioacetals
Bognar, Sabine,van Gemmeren, Manuel
supporting information, p. 4859 - 4863 (2021/02/03)
Dithioacetals are a frequently used motif in synthetic organic chemistry and have recently seen increasing attention as structural motif in promising antiviral agents against plant pathogens. Most existing reports, however, only discuss symmetrical dithioacetals. Examples of mixed dithioacetals are scarce and no general method for the selective synthesis of these compounds exists. Herein, a synthetically simple general one-step protocol was developed for the synthesis of a broad range of unsymmetrical dithioacetals consisting of one aromatic and one aliphatic thiol moiety from the corresponding aldehyde/thiol mixture. The mixed S,S-acetals were obtained in high yields, and a great variety of functional groups was tolerated. Kinetic control enabled an excellent selectivity in regard to the unsymmetrical dithioacetal.
Dithioacetalization or thioetherification of benzyl alcohols using 9-mesityl-10-methylacridinium perchlorate photocatalyst
Pramanik, Milan,Choudhuri, Khokan,Mathuri, Ashis,Mal, Prasenjit
supporting information, p. 10211 - 10214 (2020/09/21)
We report herein the use of 9-mesityl-10-methylacridinium perchlorate as the visible-light photocatalyst for dithioacetalization or thioetherification of benzyl alcohols in one pot using aerial dioxygen as a terminal oxidant. EPR analysis and Stern-Volmer
Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes
Vale, Joao R.,Rimpil?inen, Tatu,Siev?nen, Elina,Rissanen, Kari,Afonso, Carlos A. M.,Candeias, Nuno R.
, p. 1948 - 1958 (2018/02/23)
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
A Transition-Metal-Free and Base-Mediated Carbene Insertion into Sulfur-Sulfur and Selenium-Selenium Bonds: An Easy Access to Thio- and Selenoacetals
Arunprasath, Dhanarajan,Sekar, Govindasamy
, p. 698 - 708 (2017/02/23)
A transition-metal-free and base-mediated carbene insertion across sulfur-sulfur and selenium-selenium bonds has been developed by employing N-tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenol-free protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one-pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated. (Figure presented.).
Cyanuric chloride-catalyzed thioacetalization for organocatalytic synthesis of thioacetals
Liu, Yaqin
, p. 679 - 682 (2016/05/09)
The thioacetalization of aromatic aldehydes has been realized with broad diversity in the presence of various thiols and thiophenols using cyanuric chloride as an organocatalyst.
Ethyl lactate mediated thioacetalization of aldehydes at ambient temperature
Wan, Jie-Ping,Jing, Yanfeng,Liu, Yunyun
, p. 1302 - 1305 (2016/09/28)
Dithioacetalization reactions of aldehydes with thiols/thiophenols have been successfully achieved at room temperature by employing the green, bio-based ethyl lactate as the reaction medium. By means of this sustainable approach, a class of dithioacetals has been acquired with high diversity and efficiency.
Dithioacetal Exchange: A New Reversible Reaction for Dynamic Combinatorial Chemistry
Orrillo, A. Gastón,Escalante, Andrea M.,Furlan, Ricardo L. E.
supporting information, p. 6746 - 6749 (2016/05/11)
Reversibility of dithioacetal bond formation is reported under acidic mild conditions. Its utility for dynamic combinatorial chemistry was explored by combining it with orthogonal disulfide exchange. In such a setup, thiols are positioned at the intersection of both chemistries, constituting a connecting node between temporally separated networks. In reverse: Reversibility of dithioacetal bond formation is reported under acidic mild conditions (see figure). Its utility for dynamic combinatorial chemistry was explored by combining it with orthogonal disulfide exchange. In such a setup, thiols are positioned at the intersection of both chemistries, constituting a connecting node between temporally separated networks.
Reduction of titanocene dichloride with dysprosium: Access to a stable titanocene(II) equivalent for phosphite-free Takeda carbonyl olefination
Bousrez,Déchamps,Vasse,Jaroschik
supporting information, p. 9359 - 9362 (2015/06/16)
The reduction of titanocene dichloride with dysprosium yields a new titanocene(ii) equivalent without the need for further stabilising ligands. This reagent can be employed in combination with dithioacetals for the olefination of different carbonyl groups and allows for a simplified all-in-one procedure.
Rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles with disulfides: An entry to diverse transformation of terminal alkynes
Zhang, Hao,Wang, Hui,Yang, Haijun,Fu, Hua
supporting information, p. 6149 - 6153 (2015/06/08)
An efficient and useful rhodium-catalyzed denitrogenative thioacetalization of N-sulfonyl-1,2,3-triazoles has been developed for the first time. The protocol uses readily available N-sulfonyl-1,2,3-triazoles and diaryl disulfides as the starting materials. The corresponding hydrolytic and reductive products with thioacetals were obtained in good to excellent yields, and the reactions were carried out easily under mild conditions with tolerance of some functional groups. Furthermore, the generated thioacetals could be transformed into some useful compounds. Therefore, the present method provides a novel and valuable strategy for the diverse transformation of alkynes.
Efficient and chemoselective acetalization and thioacetalization of carbonyls and subsequent deprotection using InF3 as a reusable catalyst
Madabhushi, Sridhar,Mallu, Kishore Kumar Reddy,Chinthala, Narsaiah,Beeram, China Ramanaiah,Vangipuram, Venkata Sairam
experimental part, p. 697 - 701 (2012/02/15)
An efficient and chemoselective method for preparation of acetals and dithioacetals of aldehydes and their deprotection under catalysis of InF 3 is described.
