Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
J Am Chem Soc. 2022 Feb 2;144(4):1986-1992. doi: 10.1021/jacs.1c12649. Epub 2022 Jan 21.
We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel systems, does not utilizes the metal for the activation of the alkyl electrophile. Instead, this strategy exploits the halogen-atom-transfer ability of α-aminoalkyl radicals to convert secondary alkyl iodides into the corresponding alkyl radicals that then are coupled with aryl, vinyl, alkynyl, benzyl, and allyl boronate species. These novel coupling reactions feature a simple setup and conditions (1 h at room temperature) and facilitate access to privileged motifs targeted by the pharmaceutical sector.
我们在此报告了一种在铜催化剂存在下实现碘代烷烃与芳基硼酸发生铃木-宫浦型交叉偶联反应的全新方法。与基于钯和镍体系的先前方法不同，该过程不利用金属来活化烷基亲电试剂。相反，该策略利用α-氨基烷基自由基的卤素原子转移能力将仲烷基碘化物转化为相应的烷基自由基，然后与芳基、乙烯基、炔基、苄基和烯丙基硼酸物种进行偶联。这些新颖的偶联反应具有简单的反应条件（在室温下 1 小时），并且有利于获得制药领域关注的优势结构。
