A Versatile Method for Suzuki Cross‐Coupling Reactions of Nitrogen Heterocycles

Abstract

A wide‐ranging study of Suzuki reactions which use nitrogen‐containing heterocycles is described (see scheme; dba=dibenzylideneacetone, Cy=cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2‐ and OH‐substituted substrates), and efficient even with unactivated aryl chlorides.

Chromophoric Lewis Base Adducts of Methyltrioxorhenium: Synthesis, Catalysis and Photochemistry

“…Purification was done by column chromatography on silica gel. The synthesis of ligands 4-7 was based on the Suzuki cross coupling mechanism described by Fu et al [36] The heteroaryl boronic acid reacted with an aryl bromide in refluxing dioxane, whereas the reaction was catalysed by [Pd 2 (dba) 3 ] (dba = dibenzylideneacetone), PCy 3 and K 3 PO 4 (aq.). Subsequent purification steps included filtration, extraction of the filtrate and column chromatography.…”

Pyrazole Synthesis Using a Titanium‐Catalyzed Multicomponent Coupling Reaction and Synthesis of Withasomnine

“…[23] The pyrazole was prepared in 8% yield by Suzuki coupling of 5-B(OH) 2 -pyrazole and PhCl. [24] Kumada coupling of 1-trityl-4-bromopyrazole and PhMgBr catalyzed by PdCl 2 A C H T U N G T R E N N U N G (dppf) is high yielding but requires 4 steps from pyrazole. [25] We also applied this methodology to the synthesis of the natural product withasomnine, which has been prepared using a diverse array of routes.…”

Influence of Substituted Pyridine Rings on Physical Properties and Electron Mobilities of 2-Methylpyrimidine Skeleton-Based Electron Transporters

“…[ 11 ] The resulting tetrachloride ( 3 ) was coupled with an excess of 3-pyridine boronate ester ( 4 ) or 4-pyridine boronate ester ( 5 ) to afford B3PyMPM in 77% yield and B4PyMPM in 67% yield, respectively. [ 12 ] On the other hand, the 2-pyridine derivative, B2PyMPM, was prepared via the Miyaura-Ishiyama borylation of 3 with bis(pinacolato)diboron ( 6 ). The tetraboronate ester ( 7 ) was obtained in 61% yield.…”