32588-84-4Relevant articles and documents
Nickel-Catalyzed C(sp3)-C(sp3) Cross-Electrophile Coupling of in Situ Generated NHP Esters with Unactivated Alkyl Bromides
Kang, Kai,Weix, Daniel J.
supporting information, p. 2853 - 2857 (2022/05/03)
The formation of C(sp3)-C(sp3) bonds by cross-coupling remains a challenge in synthesis. Here, we demonstrate a two-step, one-pot protocol for the in situ generation of N-hydroxyphthalimide esters and their nickel-catalyzed cross-electrophile coupling with unactivated alkyl bromides for the construction of 1°/1 ° C(sp3)-C(sp3) bonds. The conditions tolerate an array of functional groups, and mechanistic studies indicate that both substrates are converted to alkyl radicals during the reaction.
Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols
Arentsen, Katherine,Caddick, Stephen,Cloke, F. Geoffrey N.,Herring, Adam P.,Hitchcock, Peter B.
, p. 3511 - 3515 (2007/10/03)
A simple new protocol for the high yielding Suzuki-Miyaura cross-couplings of aryl chlorides with aryl boronic acids using a palladium/imidazolium salt catalytic system is presented. The first examples of a palladium/imidazolium salt protocol for sp3-sp3 Suzuki-Miyaura couplings of alkyl halides are also disclosed.
Mechanism of the Solution-Phase Reaction of Alkyl Sulfides Atomic Hydrogen. Reduction via a 9-S-3 Radical Intermediate
Tanner, Dennis D.,Koppula, Sudha,Kandanarachchi, Pramod
, p. 4210 - 4215 (2007/10/03)
The low selectivity of benzyl alkyl sulfide fragmentation subsequent to its reaction with atomic hydrogen is indicative of a reaction that proceeds via an early transition state. The competitive reduction of a series of substituted-benzyl alkyl sulfides was insensitive to the substituent on the aromatic ring (ρ = -0.13, r = 0.99). The relative rates of fragmentation of a series of the substituted-benzyl alkyl sulfides gave a V-shaped Hammett plot. Both electron-donating and electron-withdrawing groups destabilized the transition state (ρ = +0.99, r = 0.999; ρ = -0.82, r = 0.992). Since the relative rates of disappearance of the alkyl benzyl sulfides are not substituent dependent, but the relative rates of fragmentation are, a 9-S-3 intermediate is preferred as the structure leading to products.