Abstract
Recently, a number of papers have emerged demonstrating copper-catalyzed alkylation reactions of electron-rich small molecules. The processes are generally thought to be related to long established atom-transfer radical reactions. However, unlike classical reactions, these new transformations lead to simple alkylation products. This short review will highlight recent advances in alkylations of nitronate anions, alkenes and alkynes, as well as discuss current mechanistic understanding of these novel reactions.
Highlights
Atom transfer radical (ATR) reactions are extremely useful in organic synthesis and polymer chemistry [1]
We envisioned that the catalytic generation of an alkyl radical under copper catalysis in the presence of a nitronate anion could lead to C-alkylated products
Various multidentate amine ligands, which are commonly used in ATR reactions, were not effective in the reaction, affording low yields of product and significant amounts of products resulting from O-alkylation (Scheme 2). β-Diketimine ligands were determined to be highly effective for the reaction, providing high yields of C-alkylated products and only trace amounts of O-alkylated products
Summary
Atom transfer radical (ATR) reactions are extremely useful in organic synthesis and polymer chemistry [1]. We envisioned that the catalytic generation of an alkyl radical under copper catalysis in the presence of a nitronate anion could lead to C-alkylated products. Radical is formed by transfer of a bromine atom from the alkyl halide to the copper catalyst. One of the burgeoning areas of copper-catalyzed cross-coupling chemistry is the alkenylation of alkyl halide substrates.
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