Aromatic Mercuration

Abstract

Mercuration is of sufficient general applicability and importance in the aromatic series tobe regarded as a typical substitution reaction, like nitration, sulfonation, or

3-Fluoro-2-mercuri-6-methylaniline Nucleotide as a High-Affinity Nucleobase-Specific Hybridization Probe

“…In the present study, a methylcytosine analogue 3-fluoro-6-methylanilinenucleotide ( F in Figure ) was prepared and incorporated into an oligonucleotide, which with the o/p- directing 1-amino and 3-fluoro group allowed facile mercuration at C2 − ( F–Hg in Figure ) and Hg­(II)-mediated base pairing, consequently. Interestingly this probe showed markedly increased duplex stability that was also strongly specific to the complementary nuclebases.…”

2-Trifluoromethyl-6-mercurianiline Nucleotide, a Sensitive 19F NMR Probe for Hg(II)-mediated Base Pairing

“…In the present work, we incorporated a trifluoromethyl group to the mercurianiline nucleoside (Figure ). The trifluoromethyl group with three chemically equivalent 19 F nuclei at C2 acts as a sensitive 19 F spin label, − but it points out toward the major groove and, hence, should not contribute much on the stability, base pairing, or conformation of the double helices formed. − This nucleotide analogue was expected to provide valuable 19 F NMR-based information on Hg­(II)-mediated base pairs even at micromolar concentrations. To evaluate these hypotheses, phosphoramidite building block 3 was synthesized and incorporated into an oligonucleotide by automated solid phase synthesis.…”

A push–pull azobenzene is mercurated twice at the ring with less electron density

“…(2)). Activated aromatic molecules easily react with mercury(II) oxide, chloride, acetate or trifluoroacetate, in increasing order of reactivity [15].…”