1369625-63-7Relevant academic research and scientific papers
Twofold unsymmetrical C-H functionalization of PyrDipSi-substituted arenes: A general method for the synthesis of substituted meta-halophenols
Sarkar, Dhruba,Melkonyan, Ferdinand S.,Gulevich, Anton V.,Gevorgyan, Vladimir
, p. 10800 - 10804 (2013)
And the world is your oyster Sequential halogenation/oxygenation reactions of 2-diisopropylsilylpyrimidine-substituted arenes provide a general and efficient synthesis of substituted meta-halophenols from simple aryl iodides (see scheme; Piv=pivaloyl). The products are poised to undergo diverse C-C, C-N, and C-O bond-forming reactions that enable the transformation of their framework and the introduction of valuable functionalities. Copyright
Synthesis of Active Hexafluoroisopropyl Benzoates through a Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C?H Alkoxycarbonylation Reaction
Wang, Yang,Gevorgyan, Vladimir
supporting information, p. 3191 - 3195 (2017/03/17)
A PdII-catalyzed ortho C?H alkoxycarbonylation reaction of aryl silanes toward active hexafluoroisopropyl (HFIP) benzoate esters has been developed. This efficient reaction features high selectivity and good functional-group tolerance. Notably, given the general nature of the silyl-tethered directing group, this method delivers products bearing two independently modifiable sites. NMR studies reveal the presence of hydrogen bonding between HFIP and a pyrimidine nitrogen atom of the directing group, and it is thought to be crucial for the success of this alkoxycarbonylation reaction.
Pd-Catalyzed C?H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group
Sarkar, Dhruba,Gevorgyan, Vladimir
supporting information, p. 11201 - 11204 (2016/08/03)
An efficient Pd-catalyzed ortho-C?H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C?H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.
Double-fold C-H oxygenation of arenes using PyrDipSi: A general and efficient traceless/modifiable silicon-tethered directing group
Gulevich, Anton V.,Melkonyan, Ferdinand S.,Sarkar, Dhruba,Gevorgyan, Vladimir
supporting information; experimental part, p. 5528 - 5531 (2012/05/20)
The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.
