Icosahedral m-Carboranes Containing Exopolyhedral B–Se and B–Te Bonds

Autor:	Ta-Chung Ong, Alexander M. Spokoyny, Harrison A. Mills, Milan Gembicky, Fadi Alsarhan, Arnold L. Rheingold
Rok vydání:	2021
Předmět:	Substitution reaction Chemistry Icosahedral symmetry chemistry.chemical_element Medicinal chemistry Article Inorganic Chemistry Nucleophile Nucleophilic aromatic substitution Reagent Electrophile Carborane Molecule Reactivity (chemistry) Physical and Theoretical Chemistry Palladium
Zdroj:	Inorg Chem
ISSN:	1520-510X 0020-1669
Popis:	Chalcogen-containing carboranes have been known for several decades and possess stable exopolyhedral B(9)-Se and B(9)-Te σ bonds despite the electron-donating ability of the B(9) vertex. While these molecules are known, little has been done to thoroughly evaluate their electrophilic and nucleophilic behavior. Herein, we report an assessment of the electrophilic reactivity of meta-carboranyl selenyl (II), tellurenyl (II), and tellurenyl (IV) chlorides and establish their reactivity pattern with Grignard reagents, alkenes, alkynes, enolates, and electron-rich arenes. These electrophilic reactions afford unique electron-rich B-Y-C (Y = Se, Te) bonding motifs not commonly found before. Furthermore, we show that meta-carboranyl selenolate, and even meta-carboranyl tellurolate, can be competent nucleophiles and participate in nucleophilic aromatic substitution reactions. Arene substitution chemistry is shown to be further extended to electron-rich species via the palladium mediated cross-coupling chemistry.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1b19ef59f7a7dee8747b1a259b300752 https://doi.org/10.1021/acs.inorgchem.1c02981 Zobrazit plný text záznamu