Twofold unsymmetrical C-H functionalization of PyrDipSi-substituted arenes: A general method for the synthesis of substituted meta-halophenols
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
Sarkar, Dhruba,Melkonyan, Ferdinand S.,Gulevich, Anton V.,Gevorgyan, Vladimir
p. 10800 - 10804
(2013/10/22)
Double-fold C-H oxygenation of arenes using PyrDipSi: A general and efficient traceless/modifiable silicon-tethered directing group
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.
Gulevich, Anton V.,Melkonyan, Ferdinand S.,Sarkar, Dhruba,Gevorgyan, Vladimir
supporting information; scheme or table
p. 5528 - 5531
(2012/05/20)
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