18001-11-1Relevant articles and documents
Palladium-Catalyzed Desilylative Acyloxylation of Silicon-Carbon Bonds on (Trimethylsilyl)arenes: Synthesis of Phenol Derivatives from Trimethylsilylarenes
Gondo, Keisuke,Oyamada, Juzo,Kitamura, Tsugio
supporting information, p. 4778 - 4781 (2015/10/12)
A strategy for desilylative acetoxylation of (trimethylsilyl)arenes has been developed in which (trimethylsilyl)arenes are converted into acetoxyarenes. The direct acetoxylation is performed in the presence of 5 mol % of Pd(OAc)2 and PhI(OCOCF3)2 (1.5 equiv) in AcOH at 80°C for 17 h. The acetoxyarenes are obtained in good to high yields (67-98%). The synthetic utility is demonstrated with a one-pot transformation of (trimethylsilyl)arenes to phenols by successive acetoxylation and hydrolysis. Furthermore, desilylative acyloxylation of 2-(trimethylsilyl)naphthalene using several carboxylic acids has been conducted.
Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes
Brenzovich Jr., William E.,Brazeau, Jean-Francois,Toste, F. Dean
supporting information; experimental part, p. 4728 - 4731 (2010/12/25)
During continuing studies with a novel oxidative gold oxyarylation reaction, arylsilanes were found to be competent coupling partners, providing further evidence for an intramolecular electrophilic aromatic substitution mechanism. While providing yields complementary to those of the previously described boronic acid methods, the use of trimethylsilanes reduces the observation of homocoupling byproducts and allows for facile intramolecular coupling reactions.
Rhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds
Tobisu, Mamoru,Kita, Yusuke,Ano, Yusuke,Chatani, Naoto
supporting information; experimental part, p. 15982 - 15989 (2009/05/16)
A rhodium-catalyzed silylation reaction of carbon - cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η2-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.
Rh(I)-catalyzed silylation of aryl and alkenyl cyanides involving the cleavage of C-C and Si-Si bonds
Tobisu, Mamoru,Kita, Yusuke,Chatani, Naoto
, p. 8152 - 8153 (2007/10/03)
The Rh(I)-catalyzed silylation of nitriles with disilanes is described. The cleavage of inert carbon-cyano and silicon-silicon bonds occurs in this catalysis. Copyright
