30934-65-7Relevant academic research and scientific papers
Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides
Potrz?saj, Aleksandra,Musiejuk, Mateusz,Cha?adaj, Wojciech,Giedyk, Maciej,Gryko, Dorota
supporting information, p. 9368 - 9376 (2021/06/28)
Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report that the vitamin B12/Ni dual-catalytic system allows for the selective synthesis of linear products under blue-light irradiation, thus complementing methodologies that give access to branched alcohols. Experimental and theoretical studies corroborate the proposed mechanism involving alkylcobalamin as an intermediate in this reaction.
Nickel-catalyzed cross-coupling of styrenyl epoxides with boronic acids
Nielsen, Daniel K.,Doyle, Abigail G.
supporting information; experimental part, p. 6056 - 6059 (2011/09/13)
Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates C-C bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X-ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving C sp 3-O bond activation. A variety of α-substituted alcohols were generated with good reaction efficiency by a multicatalytic sequence. Copyright
Regioselectivity of the rhodium-catalyzed hydroboration of vinyl arenes: Electronic twists and mechanistic shifts
Edwards, David R.,Hleba, Yonek B.,Lata, Christopher J.,Calhoun, Larry A.,Crudden, Cathleen M.
, p. 7799 - 7802 (2008/09/18)
Any substituent does it: The hydroboration of vinyl arenes with pinacol borane (HBPin) and cationic rhodium complexes selectively placed the boron proximal to the aryl rather than phenyl ring, regardless of whether this ring bears electron-donating or electron-withdrawing substituents. In competition experiments between styrene and various vinyl arenes, preferential hydroboration also occured at the substituted arene (see scheme). Hammett plots indicate a break in the mechanism. (Chemical Equation Presented).
