104-72-3Relevant articles and documents
Nickel-catalysed anti-Markovnikov hydroarylation of unactivated alkenes with unactivated arenes facilitated by non-covalent interactions
Hartwig, John F.,Nakao, Yoshiaki,Ohgi, Akito,Saper, Noam I.,Semba, Kazuhiko,Small, David W.
, (2020)
Anti-Markovnikov additions to alkenes have been a longstanding goal of catalysis, and anti-Markovnikov addition of arenes to alkenes would produce alkylarenes that are distinct from those formed by acid-catalysed processes. Existing hydroarylations are either directed or occur with low reactivity and low regioselectivity for the n-alkylarene. Herein, we report the first undirected hydroarylation of unactivated alkenes with unactivated arenes that occurs with high regioselectivity for the anti-Markovnikov product. The reaction occurs with a nickel catalyst ligated by a highly sterically hindered N-heterocyclic carbene. Catalytically relevant arene- and alkene-bound nickel complexes have been characterized, and the rate-limiting step was shown to be reductive elimination to form the C–C bond. Density functional theory calculations, combined with second-generation absolutely localized molecular orbital energy decomposition analysis, suggest that the difference in activity between catalysts containing large and small carbenes results more from stabilizing intramolecular non-covalent interactions in the secondary coordination sphere than from steric hindrance.
Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(trifluoromethyl)benzoic Acid: Photophysical Property and Application to Reduction of Carbon?Halogen Bonds as a Sensitizer
Matsubara, Ryosuke,Shimada, Toshiyuki,Kobori, Yasuhiro,Yabuta, Tatsushi,Osakai, Toshiyuki,Hayashi, Masahiko
, p. 2006 - 2010 (2016)
The photoinduced persistent intramolecular charge-transfer state of 4-carbazolyl-3-(trifluoromethyl)benzoic acid was confirmed. It showed a higher catalytic activity in terms of yield and selectivity in the photochemical reduction of alkyl halides compared to the parent carbazole. Even unactivated primary alkyl bromides could be reduced by this photocatalyst. The high catalytic activity is rationalized by considering the slower backward single-electron transfer owing to the spatial separation of the donor and acceptor subunits.
A CONVENIENT REDUCTION OF DIALKYLATED TOSYLMETHYL ISOCYANIDE
Yadav, J. S.,Reddy, P. Satyanarayana
, p. 4025 - 4028 (1984)
Dialkylated tosylmethyl isocyanides have been conveniently reduced to the corresponding hydrocarbons with lithium in liquid ammonia.This process has been succesfully utilised in the synthesis of (Z)-9-tricosene - a sex pheromone of common house fly.
Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents Using a Tetrachloroferrate with an Innocent Countercation
Hashimoto, Toru,Maruyama, Tsubasa,Yamaguchi, Takamichi,Matsubara, Yutaka,Yamaguchi, Yoshitaka
supporting information, p. 4232 - 4236 (2019/08/16)
Bis(triphenylphosphoranylidene)ammonium tetrachloroferrate, (PPN)[FeCl4] (1), was evaluated as a catalyst for cross-coupling reactions. 1 exhibits high stability toward air and moisture and is an effective catalyst for the reaction of secondary alkyl halides with aryl Grignard reagents. The PPN cation is considered as an innocent counterpart to the iron center. We have developed an easy-to-handle iron catalyst for “ligand-free” cross-coupling reactions. (Figure presented.).
Involving Single-Atom Silver(0) in Selective Dehalogenation by AgF under Visible-Light Irradiation
Wu, Wenli,Cui, Enxin,Zhang, Yun,Zhang, Chen,Zhu, Feng,Tung, Chen-Ho,Wang, Yifeng
, p. 6335 - 6341 (2019/07/04)
The dehalogenation-arylation and the hydrodehalogenation of various types of organic halides are selectively realized using AgF and visible light without any organic additives under mild conditions. Single-atom silver(0) (denoted as SAAg) serves as the catalytically active center, and the TOF of SAAg reaches 6000 h-1. This elusive activity of Ag is beyond that expected from its ionic, nano, or bulk forms.
