65063-03-8

Upstream product

• 1591-31-7 4-iodo-biphenyl 
• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 

Relevant academic research and scientific papers

C-carboranylation of a quasi-aromatic iron(II) cage complex and its organic aromatic analog by the metal-catalyzed (promoted) cross-coupling reactions

One-pot reaction a quasi-aromatic diiodoclathrochelate precursor with the carboranylating agent, generated in situ from equimolar amounts of lithium 1-ortho-carboranyl and trimethoxyborate, in the presence of a palladium catalyst afforded a ribbed-functionalized iron(II) mono-ortho-carboranoclathrochelate. Such a formation of C(carborane)C(clathrochelate) bond is accompanied by hydrodeiodination in a vicinal position and a monomethinemonocarborane macrobicyclic complex was isolated and characterized by the single crystal X-ray diffraction. The geometry of its FeN6-coordination polyhedron is intermediate between a trigonal prism and a trigonal antiprism with the distortion angle φ of 24.9 and the height h of this polyhedron is equal to 2.32 A?; FeN distances vary from 1.889(2) to 1.921(2) A? and the average bite angle α is approximately 39.1. The model reaction of this carboranylating agent with 4-iodobiphenyl, giving the corresponding aryl carborane, proceeds only in vigorous reaction conditions with a palladium catalyst and copper(I) iodide as a promotor. The compounds obtained were characterized using elemental analysis, ESI and EI mass spectrometry, IR, Raman, UV-vis, 1H, 11B, 19F and 13C{ 1H} NMR spectroscopy. Thus, palladium-catalyzed Suzuki-Miyaura (copper-promoted in the case of an aryl iodide) cross-coupling reactions of a generated in situ derivative of carboranylboronic ester have been successfully used, for the first time, for one-pot synthesis of a quasi-aromatic hybrid carboranoclathrochelate with an inherent polyhedral ribbed substituent and its aromatic analog 4-(1-ortho-carboranyl)biphenyl. The developed strategy has been then found useful in the organic chemistry as a versatile approach towards carborane-based organic compounds.

Light-promoted copper-catalyzed cage C-Arylation of: O-carboranes: facile synthesis of 1-Aryl-o-carboranes and o-carborane-fused cyclics

Light-promoted, copper catalyzed cage C-H arylation of o-carboranes with aryl halides has been achieved, leading to the facile synthesis of a variety of 1-Aryl-o-carboranes and o-carborane-fused cyclics. This method has the following features: (1) using o

Palladium-Catalyzed Direct Cross-Coupling of Carboranyllithium with (Hetero)Aryl Halides

A palladium-catalyzed direct C-arylation reaction of readily available cage carboranyllithium reagents with aryl halides has been developed for the first time. This method is applicable to a wide range of aryl halide substrates including aryl iodides, aryl bromides, and heteroaromatic halides.

Nickel-catalyzed cross-coupling reactions of o-carboranyl with aryl iodides: Facile synthesis of 1-aryl-o-carboranes and 1,2-diaryl-o-carboranes

A nickel-catalyzed arylation at the carbon center of o-carborane cages has been developed, thus leading to the preparation of a series of 1-aryl-o-carboranes and 1,2-diaryl-o-carboranes in high yields upon isolation. This method represents the first examp