934-10-1Relevant articles and documents
Chiral (Macrocyclic) Sulphides as Ligands for Nickel Catalysed Carbon-Carbon Bond Formation
Lemaire, Marc,Buter, Jan,Vriesema, Bindert K.,Kellogg, Richard M.
, p. 309 - 310 (1984)
Various sulphide combinations have been synthesized and examined as ligands for the NiII catalysed cross coupling of α-phenylethylmagnesium chloride and vinyl bromide; good yields and, in some cases, modest enantiomeric excesses can be obtained
Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities
Zhang, Bing,Xu, Xin,Tao, Lei,Lin, Zhenyang,Zhao, Wanxiang
, p. 9495 - 9505 (2021/08/04)
Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.
Palladium-catalyzed tandem isomerization/hydrothiolation of allylarenes
Kathe, Prasad M.,Fleischer, Ivana
supporting information, p. 2213 - 2217 (2019/03/26)
Herein we report a tandem olefin migration/hydrothiolation of allyl benzenes facilitated by an in situ generated palladium hydride. A catalyst system composed of palladium acetate and bidentate ligand dtbpx (1,2-bis(di-tert-butylphosphinomethyl)benzene in the presence of catalytic amounts of triflic acid led to the tandem transformation, which furnished benzylic thioethers. The reaction exhibits high regioselectivity and can be conducted under mild conditions. The robustness of the catalyst is displayed through reactions with coordinating thiols.