1,2-Dibromotetrachloroethane: An Ozone-Friendly Reagent for the in Situ Ramberg–Bäcklund Rearrangement and Its Use in the Formal Synthesis of E-Resveratrol

Abstract

Dibromotetrachloroethane (C(2)Br(2)Cl(4)) is demonstrated as a halogenating reagent for the one-pot conversion of sulfones to alkenes by way of the Ramberg-Bäcklund rearrangement. Dibromotetrachloroethane successfully replaces known ozone depleting agents CCl(4), CBr(2)F(2) and C(2)Br(2)F(4). A formal synthesis of E-resveratrol is demonstrated using C(2)Br(2)Cl(4).

Palladium‐Catalyzed Direct ortho‐C–H Bond Sulfonylation and Halogenation of Phthalazine‐1,4‐diones

“…At the outset of our study, we disclose a direct Pd(II)‐catalyzed C–H bond activation followed by cross‐coupling with aryl sulfonyl chlorides to produce a N ‐heterocyclic aromatic sulfones, as these structures have proven to be important structural motifs in a wide range of pharmaceutical molecules, including inhibitors of polynucleotide repeat‐associated RNA, prevention of heart failure, anti‐tumor, antiviral,, antibacterial, bone disorders . On the other hand, they are useful synthetic intermediates in organic reactions such as Ramberg–Bäcklund rearrangement, and Julia olefination , . Inspired by the work of Sun, We initiated our investigation on the model reaction of 2‐phenyl‐2,3‐dihydrophthalazine‐1,4‐dione ( 1a ) with benzenesulfonyl chloride ( 2a ) to optimize the critical reaction parameters (Table ).…”

Palladium-Catalyzed Semihydrogenation of Alkynes with EtOH: Highly Stereoselective Synthesis of E- and Z-Alkenes

“…13 C NMR (100 MHz, CDCl 3 ):  = 160.1, 138.9, 137.4, 129.8, 129.2, 128.8, 128.7, 127.8, 126.7, 119.4, 113.5, 111.9, 55.4. 27 Yellow solid; yield: 22.8 mg (95%).…”

Sulfide, sulfoxide and sulfone bridged acyclic nucleoside phosphonates as inhibitors of the Plasmodium falciparum and human 6-oxopurine phosphoribosyltransferases: Synthesis and evaluation

“…were treated with excess of MCPBA in dichloromethane [33] and then the resulting sulfones 11a and 12a were subjected to ester cleavage to form target compounds 13a and 14a (Scheme 2).…”