Alkyl Radical Generation from Alkylboronic Pinacol Esters through Substitution with Aminyl Radicals
作者:Zhe Wang、Nick Wierich、Jingjing Zhang、Constantin G. Daniliuc、Armido Studer
DOI:10.1021/jacs.3c01129
日期:2023.4.26
Alkylboronic pinacol esters (APEs) are highly versatile reagents in organic synthesis. However, the direct generation of alkyl radicals from commonly used, bench-stable APEs has not been well explored. In this communication, alkyl radical generation from APEs through reaction with aminyl radicals is reported. The aminyl radicals are readily generated by visible-light-induced homolytic cleavage of the
烷基硼频哪醇酯 (APE) 是有机合成中用途广泛的试剂。然而,从常用的、实验室稳定的 APEs 直接产生烷基自由基的方法尚未得到很好的探索。在此通讯中,报道了 APE 通过与氨基自由基反应生成烷基自由基。氨基自由基很容易通过可见光诱导的 N-亚硝胺中 N-N 键的均裂裂解产生,而 C 自由基的产生通过硼的核均裂取代发生。作为一项应用,提出了在温和条件下烯烃与 APE 和N-亚硝胺的高效光化学自由基烷基肟化反应。范围广泛的一级、二级和三级 APEs 参与了这种很容易扩大规模的转变。