Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via Ti<sup>III</sup>-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product
The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted b...
The synthesis and nucleophilic addition reactions of diastereoisomeric title epoxides cis-7 and tran...
Reductive ring-opening of epoxides is a green pathway for synthesizing highly value-added alcohols. ...
Thesis (Ph. D.)--University of Rochester. Department of Chemistry, 2015.In this thesis, nickel-catal...
This thesis explores the effects of tuning the ancillary phosphine ligands of low-valent nickel comp...
In recent years, the Jarvo lab has developed the field of stereospecific nickel-catalyzed cross-coup...
Cross-coupling (XC) reactions have had a lasting impact on the way synthetic organic chemists approa...
The cross-coupling of epoxides with acyl chlorides or anhydrides by a nickel/titanocene dual catalyt...
By applying a catalytic amount of indium trichloride, regioselective ring-opening of epoxides to β-h...
The regioselective opening of epoxides with organotin oxides 1 and 2, in presence of halogenated alc...
While palladium-catalyzed cross-coupling reactions have unquestionably transformed synthetic organic...
The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is rep...
Thesis (Ph. D.)--University of Rochester. Department of Chemistry, 2017.Cross – electrophile couplin...
Palladium- and nickel-catalyzed cross-coupling reactions are widely used tools for constructing carb...
A nickel-catalyzed cross-electrophile coupling reaction between benzyl alcohols and aryl halides has...
The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted b...
The synthesis and nucleophilic addition reactions of diastereoisomeric title epoxides cis-7 and tran...
Reductive ring-opening of epoxides is a green pathway for synthesizing highly value-added alcohols. ...
Thesis (Ph. D.)--University of Rochester. Department of Chemistry, 2015.In this thesis, nickel-catal...
This thesis explores the effects of tuning the ancillary phosphine ligands of low-valent nickel comp...
In recent years, the Jarvo lab has developed the field of stereospecific nickel-catalyzed cross-coup...
Cross-coupling (XC) reactions have had a lasting impact on the way synthetic organic chemists approa...
The cross-coupling of epoxides with acyl chlorides or anhydrides by a nickel/titanocene dual catalyt...
By applying a catalytic amount of indium trichloride, regioselective ring-opening of epoxides to β-h...
The regioselective opening of epoxides with organotin oxides 1 and 2, in presence of halogenated alc...
While palladium-catalyzed cross-coupling reactions have unquestionably transformed synthetic organic...
The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is rep...
Thesis (Ph. D.)--University of Rochester. Department of Chemistry, 2017.Cross – electrophile couplin...
Palladium- and nickel-catalyzed cross-coupling reactions are widely used tools for constructing carb...
A nickel-catalyzed cross-electrophile coupling reaction between benzyl alcohols and aryl halides has...
The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted b...
The synthesis and nucleophilic addition reactions of diastereoisomeric title epoxides cis-7 and tran...
Reductive ring-opening of epoxides is a green pathway for synthesizing highly value-added alcohols. ...