21078-90-0Relevant academic research and scientific papers
Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes
Logan, Kaitlyn M.,Sardini, Stephen R.,White, Sean D.,Brown, M. Kevin
, p. 159 - 162 (2018)
A Ni-catalyzed method for arylboration is disclosed. The method allows for highly stereoselective arylboration of unactivated alkenes. The reactions utilize a simple Ni-catalyst and work with a broad range of alkenes and aryl bromides. The products represent useful intermediates for chemical synthesis due to the versatility of the C-B bond. Preliminary mechanistic details of the method are also disclosed.
Palladium/TY-Phos-Catalyzed Asymmetric Intermolecular α-Arylation of Aldehydes with Aryl Bromides
Li, Wenbo,Liu, Feng,Pan, Zhangjin,Wu, Hai-Hong,Zhang, Junliang,Zhu, Shuai
, p. 18542 - 18546 (2021/07/21)
Despite much progress has been made in the asymmetric α-arylation reactions of cyclic ketones, lactones and lactams, the enantioselective α-arylation of acyclic carbonyl compounds lagged much behind due to the in situ generated Z/E-enolate intermediates l
Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: Co-catalysis controls regioselectivity
Zhao, Yang,Weix, Daniel J.
supporting information, p. 48 - 51 (2014/01/23)
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 TiIII-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
Synthesis of optically active β- Or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents
Guduguntla, Sureshbabu,Fananas-Mastral, Martin,Feringa, Ben L.
, p. 8274 - 8280 (2013/09/24)
An efficient one-pot synthesis of optically active β-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral γ-alkyl-substituted alcohols.
Phosphine-directed stereo- and regioselective Ni-catalyzed reactions of Grignard reagents with allylic ethers
Didiuk, Mary T.,Morken, James P.,Hoveyda, Amir H.
, p. 1117 - 1130 (2007/10/03)
Studies on the directed regio- and stereoselective Ni-catalyzed allylic substitution reactions involving methyl-and phenylmagnesium bromides and various acyclic and cyclic allylic ethers are reported. In the presence of a properly positioned internal Lewis base, C-C bonds can be formed catalytically and with excellent levels of selectivity. Internal chelation allows Ni-catalyzed C-C bond forming reactions that are otherwise non-selective, sluggish, or do not occur at all, to proceed to completion readily, in excellent yields, at ambient temperature and with high regio- and stereocontrol. Directed alkene isomerization highlights an especially attractive feature of the metal-catalyzed alkylation strategy: because the initial product contains a prostereogenic site that remains within reach of the internal Lewis base, it can be subjected to additional directed stereoselective manipulations.
