Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Org Lett. 2021 Jun 4;23(11):4250-4255. doi: 10.1021/acs.orglett.1c01207. Epub 2021 May 17.
A general aminoalkylation of aryl halides was developed, overcoming intolerance of free amines in nickel-mediated C-C coupling. This transformation features broad functional group tolerance and high efficiency. Taking advantage of the fast desilylation of α-silylamines upon single-electron transfer (SET) facilitated by carbonate, α-amino radicals are generated regioselectively, which then engage in nickel-mediated C-C coupling. The reaction displays high chemoselectivity for C-C over C-N bond formation. Highly functionalized pharmacophores and peptides are also amenable.
发展了一种芳基卤化物的通用胺烷基化方法，克服了镍介导的 C-C 偶联中对游离胺的不兼容性。该转化具有广泛的官能团容忍度和高效率。利用碳酸盐促进的单电子转移 (SET) 快速脱硅，α-硅基胺选择性地生成α-氨基自由基，然后与镍介导的 C-C 偶联。该反应对 C-C 键形成具有高的化学选择性，而对 C-N 键形成则选择性较低。高度功能化的药效团和肽也适用。
