KI/TBHP-mediated oxidative cross-coupling of enamines and carboxylic acids under metal-free conditions: a facile access to functionalized 2H-azirines

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• 作者：Xiyan Duan^a ; ; Xianglei Kong^b ; Xiaoyong Zhao^a ; Kun Yang^a ; Huiyun Zhou^a ; DongJu Zhou^a ; Yanping Zhang^a ; Jianwei Liu^c ; Junying Ma^a ; ; Ning Liu^a ; Zhicheng Wang^a
• 关键词：YOOGERSDPNHSJA-UHFFFAOYSA-N ; ZOMQJDVZWNTMOE-UHFFFAOYSA-N ; MTPIOMWQHMWXTG-UHFFFAOYSA-N ; ILGKAYDVDAXLTQ-UHFFFAOYSA-N ; LPJVPISIMBIPKD-UHFFFAOYSA-N ; GWOSZYSUUNJTKR-UHFFFAOYSA-N ; QQODKHIAPGCWDY-UHFFFAOYSA-N ; COJUSFSBPCOAKG-UHFFFAOYSA-N ; OYYZIUQHYVJGNP-UHFFFAOYSA-N ; FUCFTHSWXYLALH-UHFFFAOYSA-N ; AGKMXSLIAFABRQ-UHFFFAOYSA-N ; OPBRUAMQMCZYJN-UHFFFAOYSA-N ; SKMJDUIWPVRMHG-UHFFFAOYSA-N ; SKMJDUIWPVRMHG-UHFFFAOYSA-N ; HJAFNLYCYDBHNZ-UHFFFAOYSA-N ; QJNVSCOMPJHEPA-UHFFFAOYSA-N ; OHMUUZLXZGWULB-UHFFFAOYSA-N ; PFWSLGI
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：30 March 2016
• 年：2016
• 卷：57
• 期：13
• 页码：1446-1450
• 全文大小：1889 K

文摘

KI/TBHP-mediated oxidative cross coupling of enamines with carboxylic acids has been realized for the synthesis of functionalized 2H-azirines through the azirination of enamine intermediates. The metal-free strategy has several notable features, including the formation of C–O and C–N bonds in a one-pot procedure, broad functional group tolerance, good reaction yields, short reaction time, and high atom economy. It is the first example for direct formation of functionalized 2H-azirines via KI/TBHP-mediated intermolecular cross-coupling of enamines and carboxylic acids.