863560-55-8Relevant academic research and scientific papers
Microwave-assisted efficient synthesis of aryl thioethers through C-H functionalization of arenes
Liu, Yi-Chen,Lee, Chin-Fa
supporting information, p. 2320 - 2326 (2013/11/06)
Microwave-assisted iridium-catalyzed meta C-H borylation followed by copper-promoted C-S bond coupling reactions in one pot is reported. This approach enables the syntheses of aryl thioethers in short reaction times (within 2.5 hours). The system shows go
A general procedure for the regioselective synthesis of aryl thioethers and aryl selenides through C-H activation of arenes
Yi, Chih-Lun,Liu, Tsung-Jui,Cheng, Jun-Hao,Lee, Chin-Fa
, p. 3910 - 3918 (2013/07/19)
A general procedure for the synthesis of aryl thioethers and aryl selenides in one-pot through sequential iridium-catalyzed C-H borylation and copper-promoted C-S and C-Se bond formation is described. Functional groups including chloro, nitro, fluoro, trifluoromethyl, and nitrogen-containing heterocycles were all tolerated under the reaction conditions. Importantly, not only aryl thiols and selenides but also their alkyl analogs were suitable coupling partners, and the products were obtained in good yields with high meta regioselectivity. Aryl thioethers and selenides were prepared in good yields with high meta regioselectivity through sequential Ir-catalyzed C-H borylation and Cu-promoted C-S and C-Se bond formation in one pot. A wide range of functional groups were tolerated under the reaction conditions. In addition to aryl thiols and selenides, alkyl thiols and selenides were also suitable coupling partners in this reaction. Copyright
3,5-Bis(trifluoromethyl)phenyl sulfones in the Julia-Kocienski olefination - Application to the synthesis of tri- and tetrasubstituted olefins
Alonso, Diego A.,Fuensanta, Monica,Najera, Carmen
, p. 4747 - 4754 (2007/10/03)
3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 8a-d are successfully employed in the modified Julia olefination reaction with carbonyl compounds employing phosphazene base P4-tBu at room temp. in THF, affording tri- and tetrasubstituted olefins in good yi
3,5-Bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination
Alonso, Diego A.,Fuensanta, Monica,Najera, Carmen,Varea, Montserrat
, p. 6404 - 6416 (2007/10/03)
3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 7 have been employed in the Julia-Kocienski olefination reaction with carbonyl compounds. Sulfones 7 are readily prepared in high yields (64-97%) from commercially available 3,5-bis(trifluoromethyl)thiophenol through an alkylation/oxidation two-step sequence. The stability of metalated BTFP sulfones has been studied and compared with heteroaryl benzothiazol-2-yl (BT), 1-phenyl-1H-tetrazol-5-yl (PT), and 1-tert-butyl-1H-tetrazol-5-yl (TBT) sulfones 9-11 under different reaction conditions. The Julia-Kocienski olefination between alkyl BTFP sulfones 7 and a wide variety of aldehydes affords the corresponding 1,2-disubstituted alkenes and dienes in good yields and stereoselectivities. This one-pot protocol can be performed using KOH at room temperature or the phosphazene bases P2-Et and P4-t-Bu at -78 °C or rt and has been successfully used in a high-yielding and stereoselective synthesis of various methoxylated stilbenes such as trimethylated resveratrol. These new reaction conditions for the Julia-Kocienski olefination reaction have been also studied with BT, PT, and TBT sulfones, giving poorer results. Methylenation of aliphatic and aromatic aldehydes, ketones, and 1,2-dicarbonyl compounds is carried out through the modified Julia olefination using BTFP methyl sulfone 7d to give terminal alkenes and dienes. Mechanistic studies of the olefination reaction between benzyl BTFP sulfone 7a and aromatic aldehydes performed by KOH-induced Smiles rearrangement of stereodefined syn- and anit-β-hydroxyalkyl BTFP sulfones indicate that the stereocontrol of the reaction is determined in the elimination step. 2005 American Chemical Society.
