KI/TBHP-mediated oxidative cross-coupling of enamines and carboxylic acids under metal-free conditions: a facile access to functionalized 2H-azirines. Issue 13 (30th March 2016)

• Record Type: Journal Article
• Authors: Duan, Xiyan; Kong, Xianglei; Zhao, Xiaoyong; Yang, Kun; Zhou, Huiyun; Zhou, DongJu; Zhang, Yanping; Liu, Jianwei; Ma, Junying; Liu, Ning; Wang, Zhicheng
• Is Part Of: Tetrahedron letters. Volume 57:Issue 13(2016)
• Page Start: 1446
• Page End: 1450
• Publication Date: 2016-03-30
• Subjects: 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 -- PFWSLGIABGVUGA-UHFFFAOYSA-N -- QDTVKFKLJWOBLB-UHFFFAOYSA-N; Enamines -- Carboxylic acids -- KI/TBHP-mediated -- 2H-Azirine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.02.060
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: KI/TBHP-mediated oxidative cross coupling of enamines with carboxylic acids has been realized for the synthesis of functionalized 2 H -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 2 H -azirines via KI/TBHP-mediated intermolecular cross-coupling of enamines and carboxylic acids.