4352-39-0Relevant articles and documents
Titanium(IV) Chloride-Catalyzed Photoalkylation via C(sp3)-H Bond Activation of Alkanes
Yamane, Mina,Kanzaki, Yamato,Mitsunuma, Harunobu,Kanai, Motomu
supporting information, p. 1486 - 1490 (2022/03/01)
Despite the sophistication of C-H functionalization as one of the most powerful tools in organic synthesis, methodology for performing hydrogen-atom transfer of unactivated alkanes remains rather scarce. Herein, we describe chlorine radical-catalyzed C(sp3)-H photoalkylation using titanium(IV) chloride via a ligand-to-metal charge transfer process. Enabled by the unique properties of this abundant metal salt, the reaction not only effected the coupling of various alkanes with radical acceptors but also was shown to be applicable to direct photoalkylation of aromatic ketones.
Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation
Magre, Marc,Paffenholz, Eva,Maity, Bholanath,Cavallo, Luigi,Rueping, Magnus
supporting information, p. 14286 - 14294 (2020/09/15)
A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.
Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Ganiu, Moshood O.,Cleveland, Alexander H.,Paul, Jarrod L.,Kartika, Rendy
supporting information, p. 5611 - 5615 (2019/08/01)
The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.
