Organic Chemistry Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune-411008, India.
Org Lett. 2012 Dec 21;14(24):6238-41. doi: 10.1021/ol302997q. Epub 2012 Dec 10.
A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.
本文报道了一种高效的 1,2-苯醌与芳炔的 Diels-Alder 反应新协议。通过氟化物诱导的 2-（三甲基甲硅烷基）芳基三氟甲磺酸酯的 1,2-消除生成的芳炔与 1,2-苯醌发生易于进行的 Diels-Alder 反应，以中等至优异的收率得到二氧杂苯并双环辛二烯。此外，该方法已应用于苯并喹喔啉-barrelene 和萘衍生物的一锅合成。
