7116-97-4Relevant articles and documents
Nickel-catalyzed alkyl-alkyl cross-coupling reactions of non-activated secondary alkyl bromides with aldehydes as alkyl carbanion equivalents
Zhu, Chenghao,Zhang, Junliang
, p. 2793 - 2796 (2019/03/06)
A novel nickel-catalyzed alkyl-alkyl cross coupling of non-activated secondary alkyl bromides with aldehydes via hydrazone intermediates has been developed. Aldehydes as alkyl carbanion equivalents replace traditional organometallic reagents. This coupling occurs on the carbon of the hydrazone rather than the nitrogen. In addition, non-activated primary and tertiary alkyl bromides also undergo the cross-coupling reaction to form new C(sp3)-C(sp3) bonds in moderate yields.
UVA- and Visible-Light-Mediated Generation of Carbon Radicals from Organochlorides Using Nonmetal Photocatalyst
Matsubara, Ryosuke,Yabuta, Tatsushi,Md Idros, Ubaidah,Hayashi, Masahiko,Ema, Fumitoshi,Kobori, Yasuhiro,Sakata, Ken
, p. 9381 - 9390 (2018/07/25)
Carbon radicals are reactive species useful in various organic transformations. The C-X bond cleavage of organohalides by photoirradiation is a common method to generate carbon radicals in a controlled fashion. The use of organochloride substrates is still a formidable challenge due to the low reduction potential and the high dissociation energy of the C-Cl bond. In this report, we address these issues by using a nonmetal organic molecule with a relatively simple structure as a photocatalyst. In this catalyst (bis(dimethylamino)carbazole), the amino groups increase both the HOMO and LUMO energy levels, especially in the former. As a result, compared to the parent molecule, the new catalyst shows experimentally red-shifted absorption in the visible region and forms an excited state with better reducing capability. This photocatalyst was used in the reduction of unactivated aryl chlorides and alkyl chlorides in the presence of hydrogen atom donor at room temperature. The catalytic system can also be applied to the coupling of aryl chlorides with electron-rich arene and heteroarenes to affect the C-C bond-forming reactions. Our mechanistic study results support the assumption that carbon radicals are formed from the organochlorides via a single-electron-transfer step.
Catalytic activity of 1-methylimidazole-based phosphine ligands in the palladium-catalyzed Suzuki coupling reaction
Guan, Jin Tao,Song, Xiao Ming,Zhang, Zhi Yong,Wei, Ben Mei,Dai, Zhi Qun
, p. 87 - 89 (2015/01/30)
The catalytic activities of three N-methylimidazole-based phosphine ligands in the Suzuki coupling reaction were tested using PdCl2 as the catalyst. The results showed all three phosphine ligands exhibited excellent activity towards the Suzuki reaction, and the catalytic activity decreased with increasing number of imidazole groups.
