Sharma Arun, Dixit Vikas, Kumar Sharvan, Jain Nidhi
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, 110016 New Delhi, India.
Org Lett. 2021 May 7;23(9):3409-3414. doi: 10.1021/acs.orglett.1c00862. Epub 2021 Apr 12.
An unprecedented visible light-assisted and zinc triflate-catalyzed construction of a diaryl-substituted quaternary stereocenter is reported. 2-(4-Hydroxyphenyl)-substituted aldehydes and ketones have been prepared in moderate to high yields via multicomponent reaction of acetylene, benzoquinone (BQ), and indole/aniline/thiol. The reaction is believed to proceed via generation of -quinone methide through a [2+2] cycloaddition-retroelectrocyclization of BQ and acetylene in blue light followed by a zinc triflate-catalyzed vinylogous Michael addition reaction with nucleophiles.
报道了一种前所未有的可见光辅助和三氟甲磺酸锌催化构建二芳基取代季碳立体中心的方法。通过乙炔、苯醌（BQ）与吲哚/苯胺/硫醇的多组分反应，以中等至高产率制备了2-（4-羟基苯基）取代的醛和酮。据信该反应是通过蓝光下BQ与乙炔的[2+2]环加成-逆电环化生成醌甲基化物，然后与亲核试剂进行三氟甲磺酸锌催化的烯丙基迈克尔加成反应来进行的。
