- Visible-Light Photoredox-Catalyzed Thioacetalization of Aldehydes Under Metal-Free and Solvent-Free Conditions
-
A first visible-light photoredox-catalyzed thioacetalization of aldehydes under metal-free and solvent-free conditions is described. Under blue LED irradiation, a reactive thiyl radical was initially generated through single-electron oxidation of thiol, w
- Du, Kai,Wang, Shao-Chien,Basha, R. Sidick,Lee, Chin-Fa
-
p. 1597 - 1605
(2018/12/11)
-
- Enantio-, Regio- and Chemoselective Copper-Catalyzed 1,2-Hydroborylation of Acylsilanes
-
Enantioselective synthesis of synthetically significant (α-hydroxyallyl)silanes, (α-hydroxyaryl)silanes, and (α-hydroxyalkyl)silanes is reported. The present copper-catalyzed 1,2-selective hydroborylation of acylsilanes affords the aforementioned products
- Nagy, Audric,Collard, Laurent,Indukuri, Kiran,Leyssens, Tom,Riant, Olivier
-
supporting information
p. 8705 - 8708
(2019/06/13)
-
- A 2 - substituted - 1, 3 - dithiane derivative of the preparation method
-
The invention provides a preparation method of a 2-substituted-1,3-dithiane derivative. The preparation method comprises the following steps: adding 1,3-dithiane (CAS:505-23-7) and 1,2-dichloroethane (DCE) or dichloromethane (DCM) into a reaction bottle, adding N-chlorosuccinimide (NCS) under ice-bath condition, and stirring for 0.5-1 h to prepare a 2-chloro-1,3-dithiane solution; and adding an aldehyde or ketone compound and a lewis acid catalyst into the above solution, and reacting to prepare the 2-substituted-1,3-dithiane derivative. By using the 1,3-dithiane solid and different types of aldehyde and keto-carbonyl compounds as raw material and using one or more of ferric trichloride, boron trifluoride diethyl etherate, methanesulfonic acid, aluminum trichloride, ferrous chloride and nickel chloride as catalysts, preparation of the 2-substituted-1,3-dithiane derivative is realized. The catalysts used in the invention are cheap and easily available, dosage of the catalysts is low and pollution of the catalysts is little. The solid raw materials used in the invention can avoid use of fetid toxic 1,3-dimercaptopropane with strong volatility, and the purpose of protecting an experimenter's body and reducing environmental pollution is realized. In addition, the preparation method has advantages of mild reaction condition, high yield, simple operation and the like.
- -
-
Paragraph 0023; 0024; 0025; 0026
(2019/06/26)
-
- Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes
-
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.
- Vale, Joao R.,Rimpil?inen, Tatu,Siev?nen, Elina,Rissanen, Kari,Afonso, Carlos A. M.,Candeias, Nuno R.
-
p. 1948 - 1958
(2018/02/23)
-
- Preparing method of 2-substituted-1,3-dithiane derivative
-
The invention belongs to the technical field of organic synthesis, and particularly discloses a preparing method of a 2-substituted-1,3-dithiane derivative. The preparing method comprises the following steps of adding substrate aldehyde, 1,3-dimercaptopro
- -
-
Paragraph 0020-0026; 0084-0836
(2018/10/02)
-
- Sulfur-Directed Ligand-Free C-H Borylation by Iridium Catalysis
-
An iridium-catalyzed ortho C-H borylation reaction directed by cyclic dithioacetal moiety is disclosed. A series of borylation products were obtained in moderate to good yields under mild conditions in exclusive mono- and ortho-regioselectivity. Thus, the 1,3-dithiane or 1,3-dithiolane group serves as a remarkable effective directing group for C-H borylation without any ligand assistance. The further transformations of the borylation products are also carried out to change boryl group to other functional groups.
- Liu, Li,Wang, Guanghui,Jiao, Jiao,Li, Pengfei
-
supporting information
p. 6132 - 6135
(2017/11/24)
-
- Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations
-
Oxidative [1,2]-Brook rearrangements via hypervalent silicon intermediates induced by photoredox-catalyzed single-electron transfer have been achieved, permitting the formation of reactive radical species that can engage in alkylations and arylations.
- Deng, Yifan,Liu, Qi,Smith, Amos B.
-
supporting information
p. 9487 - 9490
(2017/07/24)
-
- Rhodium(III)-catalyzed oxidative alkenylation of 1,3-dithiane-protected arenecarbaldehydes via regioselective C-H bond cleavage
-
A Rh(III)-catalyzed direct alkenylation of 2-aryl-1,3-dithiane derivatives with alkenes has been developed. The 1,3-dithiane group can serve as an effective directing group for the exclusively monoselective alkenylation under mild oxidative conditions. Th
- Unoh, Yuto,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
-
supporting information
p. 704 - 707
(2015/03/05)
-
- Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation
-
The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by 13C NMR spectroscopy and extension to an asymmetric variant is also presented.
- Denmark, Scott E.,Cullen, Lindsey R.
-
supporting information
p. 70 - 73
(2014/01/23)
-
- Fe-catalyzed direct dithioacetalization of aldehydes with 2-chloro-1,3-dithiane
-
Present methods to synthesize 1,3-dithiane molecules require either harsh reaction conditions or highly specialized reagents. We have developed a catalytic dithioacetalization process that directly gains access to the corresponding 1,3-dithianes using aldehydes and 2-chloro-1,3-dithiane in a highly efficient manner. This methodology is beneficial due to mildness of the reaction conditions, and the dithioacetaliation process results in good to excellent yields by using 15 mol % of an iron catalyst.
- Lai, Junshan,Du, Wenbin,Tian, Lixia,Zhao, Changgui,She, Xuegong,Tang, Shouchu
-
p. 4396 - 4399
(2015/01/08)
-
- Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals
-
Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in
- Ghashang, Majid
-
p. 2837 - 2842
(2013/07/26)
-
- 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of carbonyl compounds and transdithioacetalization reactions
-
The use of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high yields in the presence of thiols.
- Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza,Zolfigol
-
p. 1047 - 1071
(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)
-
- 1,3-Dithiane derivatives as radioprotective agents
-
Compounds derived from 1,3 dithiane have been prepared and evaluated as potential antiradiation agents in mice. They are generally less toxic than their dithiolane homologs and have markedly lower radioprotective activity.
- Fernandez,Robbe,Chapat,et al.
-
p. 461 - 464
(2007/10/02)
-