727733-92-8Relevant articles and documents
Late-Stage N-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis
Shen, Yangyang,Rovis, Tomislav
supporting information, p. 16364 - 16369 (2021/10/21)
The diversity and wide availability of trialkylamines render them ideal sources for rapid construction of complex amine architectures. Herein, we report that a nickel/photoredox dual catalysis strategy affects site-selective α-arylation of various trialkylamines. Our catalytic system shows exclusive N-Me selectivity with a wide range of trialkylamines under mild conditions, even in the context of late-stage arylation of pharmaceutical compounds bearing this common structural motif. Mechanistic studies indicate the unconventional behavior of Ni catalyst upon intercepting the α-amino radicals, in which only the primary α-amino radical undergoes a successful cross-coupling process.
Modular, Self-Assembling Metallaphotocatalyst for Cross-Couplings Using the Full Visible-Light Spectrum
Reischauer, Susanne,Strauss, Volker,Pieber, Bartholom?us
, p. 13269 - 13274 (2020/12/03)
The combination of nickel and photocatalysis has unlocked a variety of cross-couplings. These protocols rely on a few photocatalysts that can only convert a small portion of visible light (500 nm) into chemical energy. The high-energy photons that excite
Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: Silyl species enable reactivity
Li, Hu,Zhao, Wenfeng,Dai, Wenshuai,Long, Jingxuan,Watanabe, Masaru,Meier, Sebastian,Saravanamurugan, Shunmugavel,Yang, Song,Riisager, Anders
, p. 5327 - 5335 (2018/12/05)
Biomass derivatives are a class of oxygen-rich organic compounds, which can be selectively upgraded to various value-added molecules by partial or complete hydrogenation over metal catalysts. Here, we show that Cs2CO3, a low-cost commercial chemical, enables the selective reduction of dicarbonyl compounds including bio-derived carboxides to monohydric esters/amides, hydroxylamines or diols with high yields (82-99%) at room temperature using eco-friendly and equivalent hydrosilane as a hydride donor. The in situ formation of silyl ether enables the developed catalytic system to tolerate other unsaturated groups and permits a wide substrate scope with high selectivities. Spectroscopic and computational studies elucidate reaction pathways with an emphasis on the role of endogenous siloxane.
