镍/光氧化还原双催化对映选择性合成 -苄基杂环
Enantioselective Synthesis of -Benzylic Heterocycles by Ni/Photoredox Dual Catalysis.
机构信息
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
出版信息
J Am Chem Soc. 2022 Nov 9;144(44):20190-20195. doi: 10.1021/jacs.2c07917. Epub 2022 Oct 26.
Abstract
An asymmetric cross-coupling of α-heterocyclic trifluoroborates with aryl bromides using Ni/photoredox dual catalysis has been developed. This C(sp)-C(sp) cross-coupling provides access to pharmaceutically relevant chiral -benzylic heterocycles in good to excellent enantioselectivity when bioxazolines (BiOX) are used as the chiral ligand. High-throughput experimentation significantly streamlined reaction development by identifying BiOX ligands for further investigation and by allowing for rapid optimization of conditions for new trifluoroborate salts.
摘要
发展了一种使用 Ni/光氧化还原双催化的α-杂环三氟硼酸盐与芳基溴化物的不对称交叉偶联反应。当使用生物恶唑啉 (BiOX) 作为手性配体时，这种 C(sp)-C(sp) 交叉偶联反应可以很好地获得具有良好对映选择性的药物相关手性 -苄基杂环。高通量实验通过确定进一步研究的 BiOX 配体，并允许快速优化新三氟硼酸盐盐的条件，极大地简化了反应开发。
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