54607-03-3Relevant articles and documents
Nickel-catalyzed Heck reaction of cycloalkenes using aryl sulfonates and pivalates
Zhou, Jianrong Steve,Huang, Xiaolei,Teng, Shenghan,Chi, Yonggui Robin
supporting information, p. 3933 - 3936 (2021/04/26)
Nickel-catalyzed Heck reaction of cycloalkenes delivers unusual conjugated arylated isomers. Nickel(0) catalysts ligated by chelating dialkylphosphines effectively activate not only aryl triflates as electrophiles, but also less reactive aryl mesylates, t
Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C?O or C?N Bond Cleavage
Yang, Ze-Kun,Wang, Dong-Yu,Minami, Hiroki,Ogawa, Hiroyuki,Ozaki, Takashi,Saito, Tatsuo,Miyamoto, Kazunori,Wang, Chao,Uchiyama, Masanobu
supporting information, p. 15693 - 15699 (2016/10/25)
Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C?O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)2] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C?N bond cleavage in the presence of a [Pd(PPh3)2Cl2] catalyst. These methods enable selective sequential functionalizations of arenes having both C?N and C?O bonds in one pot.
Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: Development of an asymmetric aza-pinacol cyclization
Rono, Lydia J.,Yayla, Hatice G.,Wang, David Y.,Armstrong, Michael F.,Knowles, Robert R.
, p. 17735 - 17738 (2014/01/06)
The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Bronsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.
