54845-36-2Relevant academic research and scientific papers
An active, general, and long-lived palladium catalyst for cross-couplings of deactivated (hetero)aryl chlorides and bromides with arylboronic acids
Hoshi, Takashi,Honma, Tomonobu,Mori, Ayako,Konishi, Maki,Sato, Tsutomu,Hagiwara, Hisahiro,Suzuki, Toshio
, p. 11513 - 11524 (2013/12/04)
An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp3)-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.
Rational exploration of N-Heterocyclic carbene (NHC) palladacycle diversity: A highly active and versatile precatalyst for suzuki-miyaura coupling reactions of deactivated aryl and alkyl substrates
Peh, Guang-Rong,Kantchev, Eric Assen B.,Er, Jun-Cheng,Ying, Jackie Y.
supporting information; experimental part, p. 4010 - 4017 (2010/08/05)
As less attention has been focussed on the design of highly efficient palladium precatalysts to ensure the smooth formation of the active catalyst for metal-mediated cross coupling reactions, we herein demonstrate that combining the bulky N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene (IPr) with cyclopalladated acetanilide as the optimal palladium precatalyst leads to superior catalytic activity compared with the state-of-the-art NHC-Pd catalysts. The complex was discovered through the evaluation of a small, rationally designed library of NHC-palladacycles prepared by a novel, practical and atom-economic method, the direct reaction of IPrHCl with palladacycle acetate dimers.
Diazotisation of aromatic amines and solvolysis of diazonium salts in ethylene glycol ethers
Ram, Ram N.,Singh, Virinder
, p. 800 - 803 (2007/10/03)
Aniline and unhindered alkyl-substituted anilines undergo solvolysis in dioxane and DME saturated with dry hydrogen chloride on diazotisation with isoamyl nitrite to give 2-(2-chloroethoxy)ethyl aryl ethers and 2-methoxyethyl aryl ethers respectively in 36-47% yields. 2,6-Dialkyl-substituted anilines give the corresponding chloro compounds as the major product along with the aryl ethers in lower yields. Diazotisation of aniline in ethylene glycol and monomethyl ethers of ethylene glycol and diethylene glycol gave the corresponding alcoholysis products in low yields. The solvolysis of aniline did not occur on diazotisation in diethyl ether or THF.
Hydrocarbons and chloroaromatics from anilines and n-butyl nitrite
Giumanini, Angelo G.,Verardo, Giancarlo,Gorassini, Fausto,Strazzolini, Paolo
, p. 311 - 316 (2007/10/02)
A single reagent, i.e. n-butyl nitrite, can be used to oxidize an aromatic amine, or the corresponding N-methylene derivative, to a diazo compound followed by its subsequent reduction to hydrocarbon in a single batch.Alternatively, a chloro derivative can be obtained if carbon tetrachloride is used as the solvent.The reactions appear to be general and complete product identification was accomplished.
Sterically Congested Molecules, 11. The 2,6-Diisopropylphenyl Substituent at C=C and C=N Groups
Knorr, Rudolf,Ruhdorfer, Jakob,Boehrer, Petra,Bronberger, Hildegard,Raepple, Edith
, p. 433 - 438 (2007/10/02)
Two series of new compounds with sterically shielded, sp2-hybridized C-α atoms are prepared from bromo(chloro)-2,6-diisopropylbenzene.The α-(2,6-diisopropylphenyl) substituent common to all of them is used as an NMR-spectroscopic indicator for
