96555-88-3Relevant articles and documents
Nickel-Mediated Trifluoromethylation of Phenol Derivatives by Aryl C?O Bond Activation
Hu, Wei-Qiang,Pan, Shen,Qing, Feng-Ling,Vicic, David A.,Xu, Xiu-Hua
, p. 16076 - 16082 (2020/07/04)
The increasing pharmaceutical importance of trifluoromethylarenes has stimulated the development of more efficient trifluoromethylation reactions. Tremendous efforts have focused on copper- and palladium-mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel-mediated trifluoromethylation of phenol derivatives with readily available trimethyl(trifluoromethyl)silane (TMSCF3). The strategy relies on PMe3-promoted oxidative addition and transmetalation, and CCl3CN-induced reductive elimination. The broad utility of this transformation has been demonstrated through the direct incorporation of trifluoromethyl into aromatic and heteroaromatic systems, including biorelevant compounds.
Formation of nickel-thiolate aggregates via reaction with CH 2Cl2
Wang, Qiang,Marr, Andrew C.,Blake, Alexander J.,Wilson, Claire,Schroeder, Martin
, p. 2776 - 2777 (2007/10/03)
Reaction of the mononuclear nickel-thiolate complex [Ni(L 1)(dppe)] with CH2Cl2 affords the novel pentanuclear complex [Ni5Cl2(L1) 4(dppe)2], while [Ni(L1)(
Preparation and reactivity of nickel(0) complexes with η2-coordinated alkynylphosphines
Bennett, Martin A.,Castro, Jeffrey,Edwards, Alison J.,Kopp, Mike R.,Wenger, Eric,Willis, Anthony C.
, p. 980 - 989 (2008/10/08)
The η2-alkynylphosphine complexes [Ni(η2-Ph2PC≡CR)(dcpe)] (R = Me (1a), CO2Me (1b), Ph (1c)), which are formed by displacement of ethylene from [Ni(C2H4)(dcpe)] by the corresponding alkynylphosphine, react with HCl (1 equiv) to give five-coordinate nickel(II) complexes, [NiCl{C(=CHR)PPh2-κP,C1}(dcpe)] (R = Me (2a), CO2Me (2b), Ph (2c)), which contain a coordinated methylenephosphanickelacyclopropane fragment. In the case of 1a, the proton adds regiospecifically at the carbon atom bearing the methyl group. This mode of addition is favored for 1b,c, but small amounts of the addition products [NiCl{η1-C(R)=CH(PPh2)}(dcpe)] (R = CO2Me (3b), Ph (3c)), arising from addition at the PPh2-bearing carbon atoms, are also formed. Unsaturated molecules such as CS2 and CO2 insert into the Ni-P bonds of complexes 2a,c to give five-membered nickelacycles. Complexes 1a, 2a,c, and 3c have been structurally characterized by X-ray diffraction analysis.