33186-68-4Relevant articles and documents
Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols
Bai, Jixiang,Wang, Tianxin,Dai, Botao,Liu, Qingchao,Yu, Peiyuan,Jia, Tiezheng
supporting information, p. 5761 - 5765 (2021/08/16)
A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Azodicarbonyl dimorpholide (ADDM): An effective, versatile, and water-soluble Mitsunobu reagent
Lanning, Maryanna E.,Fletcher, Steven
, p. 4624 - 4628 (2013/08/23)
One of the caveats of the Mitsunobu reaction is the often difficult and laborious purification of the reaction mixture. Herein, we show that azodicarbonyl dimorpholide (ADDM) is an effective and versatile Mitsunobu reagent, which, along with its reduced form ADDM-H2, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H2 may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented.
