Polar−π and Cation−π Stabilizing Interactions between Constrained Cofacial Aromatic Rings Favoring the More Sterically Hindered Diastereomer

Lavieri, Sophie; Zoltewicz, John A.

doi:10.1021/jo010537a

Cited by 30 publications

(18 citation statements)

References 34 publications

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“…15a-c). [49][50][51][52][53][54] The syn conformation was dominant for all of the compounds depicted in Figure 15a. The large upfield shielding of the 1 H-NMR methyl signals and the preference for the syn conformation can be attributed to the existence of favourable cation•••arene and CH•••areneinteractions between the positively polarised methyl substituents of one ring and electron-rich naphthalene face of the other.…”

Section: Figure 14mentioning

confidence: 95%

Molecular balances for quantifying non-covalent interactions

2010

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Molecular interactions underlie the whole of chemistry and biology. This tutorial review illustrates the use of rotameric folding molecules, topoisomers, atropoisomers, and tautomers as molecular balances for quantifying non-covalent interactions. This intramolecular approach enables a wide variety of interactions to be examined with a degree of geometric control that is difficult to achieve in supramolecular complexes. Synthetic variation of molecular balances allows the fundamental physicochemical origins of molecular recognition to be systematically examined by providing insights into the interplay of geometry and solvation on non-covalent interactions.

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Section: Figure 14mentioning

confidence: 95%

Molecular balances for quantifying non-covalent interactions

2010

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“…Compound 5 was presumably formed via oxidation of the silane to the corresponding silanols, followed by displacement of the pinacol by intramolecular substitution and hydrolysis . The C−B bond in 5 was converted to a C−C bond in a biaryl by a palladium‐catalyzed Suzuki‐coupling reaction . The C−B bond in 5 also was transformed to a C‐halogen bond (C−Br and C−Cl) and C−N bond by copper‐catalyzed and copper‐mediated processes .…”

Section: Methodsmentioning

confidence: 99%

Iridium‐Catalyzed, Silyl‐Directed, peri‐Borylation of C−H Bonds in Fused Polycyclic Arenes and Heteroarenes

Hartwig

2018

Angewandte Chemie

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peri‐Disubstituted naphthalenes exhibit interesting physical properties and unique chemical reactivity, due to the parallel arrangement of the bonds to the two peri‐disposed substituents. Regioselective installation of a functional group at the position peri to 1‐substituted naphthalenes is challenging due to the steric interaction between the existing substituent and the position at which the second one would be installed. We report an iridium‐catalyzed borylation of the C−H bond peri to a silyl group in naphthalenes and analogous polyaromatic hydrocarbons. The reaction occurs under mild conditions with wide functional group tolerance. The silyl group and the boryl group in the resulting products are precursors to a range of functional groups bound to the naphthalene ring through C−C, C−O, C−N, C−Br and C−Cl bonds.

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“…The synthesis of conformationally stable atropisomers of 1,8-diaryl or heteroaryl naphthalenes is recently reported [1,[8][9][10][11][12][13][14]. These compounds show anti-syn atropisomerism at ambient temperature.…”

Section: Introductionmentioning

confidence: 99%