1188335-75-2Relevant academic research and scientific papers
Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation
Mihai, Madalina T.,Williams, Benjamin D.,Phipps, Robert J.
, p. 15477 - 15482 (2019/10/11)
The selective functionalization of C-H bonds at the arene para position is highly challenging using transition metal catalysis. Iridium-catalyzed borylation has emerged as a leading technique for arene functionalization, but there are only a handful of strategies for para-selective borylation, which operate on specific substrate classes and use bespoke ligands or catalysts. We describe a remarkably general protocol which results in para-selectivity on some of the most common arene building blocks (anilines, benzylamines, phenols, benzyl alcohols) and uses standard borylation ligands. Our strategy hinges upon the facile conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is paired with a tetrabutylammonium cation. We hypothesize that the bulk of this cation disfavors meta-C-H borylation, thereby promoting the challenging para-selective reaction.
Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions
Montero Bastidas, Jose R.,Oleskey, Thomas J.,Miller, Susanne L.,Smith, Milton R.,Maleczka, Robert E.
supporting information, p. 15483 - 15487 (2019/10/11)
Para C-H borylations (CHB) of tetraalkylammonium sulfates and sulfamates have been achieved using bipyridine-ligated Ir boryl catalysts. Selectivities can be modulated by both the length of the alkyl groups in the tetraalkylammonium cations and the substituents on the bipyridine ligands. Ion pairing, where the alkyl groups of the cation shield the meta C-H bonds in the counteranions, is proposed to account for para selectivity. The 4,4′-dimethoxy-2,2′-bipyridine ligand gave superior selectivities.
3,3′-Disubstituted bipolar biphenyls as inhibitors of nuclear receptor coactivator binding
Weiser, Patrick T.,Williams, Anna B.,Hanson, Robert N.,Chang, Ching-Yi,McDonnell, Donald P.
, p. 6587 - 6590,4 (2012/12/12)
A series of bipolar biphenyl compounds was synthesized as proteomimetic analogs of the LXXLL penta-peptide motif responsible for the binding of coactivator proteins to the nuclear hormone receptor coactivator binding domain. These compounds were subjected
Synthesis of biphenyl proteomimetics as estrogen receptor-a coactivator binding inhibitors
Williams, Anna B.,Weiser, Patrick T.,Hanson, Robert N.,Guenther, Julian R.,Katzenellenbogen, John A.
supporting information; experimental part, p. 5370 - 5373 (2010/02/28)
"Chemical Equation Presented" A novel series of blphenyl proteomlmetic compounds were designed as estrogen receptor-α (ERα) coactivator binding Inhibitors. Synthesis was accomplished through a convergent approach, employing Suzuki coupling chemistry to li
MODULATORS OF NUCLEAR RECEPTOR CO-REGULATORY PROTEIN BINDING
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Page/Page column 56, (2009/10/22)
Disclosed are novel compounds and compositions for inhibition of androgen and estrogen receptor signaling, methods for inhibiting androgen signaling, methods for inhibiting estrogen signaling, methods for inhibiting the interaction between a co-regulatory protein and an androgen or estrogen receptor, and methods for treating cancer.
