Pfizer Worldwide Research and Development , Groton, Connecticut 06340, United States.
Pfizer Worldwide Research and Development , La Jolla, California 92037, United States.
Org Lett. 2017 Dec 15;19(24):6566-6569. doi: 10.1021/acs.orglett.7b03280. Epub 2017 Nov 28.
A mild Ru/Ni dual catalytic desulfinative photoredox C-C cross-coupling reaction of alkyl sulfinate salts with aryl halides has been developed. The optimized catalyst system, consisting of Ru(bpy)Cl, Ni(COD), and DBU, smoothly mediates the coupling of a diverse set of secondary and primary nonactivated alkyl sulfinate salts with a broad range of electron-deficient aryl bromides, electron-rich aryl iodides, and heteroaryl bromides under irradiation with blue light. The procedure is ideal for late-stage introduction of alkyl groups on pharmaceutical intermediates, and the C-C cross-coupling reaction allowed the rapid synthesis of caseine kinase 1δ inhibitor analogues via a parallel medicinal chemistry effort.
已开发出一种温和的 Ru/Ni 双催化脱硫光氧化还原 C-C 交叉偶联反应，用于芳基卤化物与烷基磺酸盐的反应。优化的催化剂体系由 Ru(bpy)Cl、Ni(COD)和 DBU 组成，可在蓝光照射下顺利介导一系列不同的仲烷基和伯非活化烷基磺酸盐与广泛的缺电子芳基溴化物、富电子芳基碘化物和杂芳基溴化物的偶联。该方法非常适合在药物中间体的后期阶段引入烷基，C-C 交叉偶联反应允许通过平行的药物化学努力快速合成酪蛋白激酶 1δ抑制剂类似物。
