2605-18-7Relevant articles and documents
Exploring the scope of nitrogen acyclic carbenes (NACs) in gold-catalyzed reactions
Bartolome, Camino,Garcia-Cuadrado, Domingo,Ramiro, Zoraida,Espinet, Pablo
, p. 3589 - 3592 (2010)
The catalytic activity of the recently reported nitrogen acyclic carbene (NAC) complexes of gold(I) has been investigated and compared with the reported activity of other gold(I) and gold(III) complexes. The complexes studied, [AuCl{C(NEt2)(NHTol-p)}], [AuCl{C(NEt2)(NHXylyl)}], and [Au(NTf2){C(NEt2)(NHXylyl)}], are very active in processes such as the rearrangement of homopropargylsulfoxides, the intramolecular hydroamination of N-allenyl carbamates, the intramolecular hydroalkoxylation of allenes, the hydroarylation of acetylenecarboxylic acid ester, and the benzylation of anisole. Although the NAC ligands have not been optimized for the reactions tested, the yields obtained are usually similar and sometimes better than those reported with other catalysts, showing that the presence of N-H bonds and the wider N-C-N angle in the NAC (as compared to the NHC) complexes are not detrimental for the catalysis. For the hydroarylation reaction (where two competing products can be formed), the NAC complexes allow favoring one over the other. For the benzylation of anisole the selectivity is complementary to that obtained using H[AuCl4] as catalyst, and depending on the substrate, the NAC gold(III) complexes outperform the activity of H[AuCl4]. On average, the reactivity found suggests that the basicity of NACs toward gold(I) is very similar to that of NHCs and higher than that of phosphines.
Indium Tribromide-Catalysed Transfer-Hydrogenation: Expanding the Scope of the Hydrogenation and of the Regiodivergent DH or HD Addition to Alkenes
Li, Luomo,Hilt, Gerhard
supporting information, p. 11221 - 11225 (2021/06/25)
The transfer-hydrogenation as well as the regioselective and regiodivergent addition of H?D from regiospecific deuterated dihydroaromatic compounds to a variety of 1,1-di- and trisubstituted alkenes was realised with InBr3 in dichloro(m)ethane. In comparison with the previously reported BF3?Et2O-catalysed process, electron-deficient aryl-substituents can be applied reliably and thereby several restrictions could be lifted, and new types of substrates could be transformed successfully in hydrodeuterogenation as well as deuterohydrogenation transfer-hydrogenation reactions.
Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
Li, Zijian,Sun, Wenxuan,Wang, Xianxu,Li, Luyang,Zhang, Yong,Li, Chao
supporting information, p. 3536 - 3543 (2021/03/08)
As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.
