Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

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• 作者：Andrey A. Mikhaylov^a ; ; Alexander D. Dilman^a ; Roman A. Novikov^a ; Yulia A. Khoroshutina^a ; Marina I. Struchkova^a ; Dmitry E. Arkhipov^b ; ^c ; Yulia V. Nelyubina^b ; Andrey A. Tabolin^a ; Sema L. Ioffe^a ;
• 关键词：Palladium-catalysis ; Cross-coupling reactions ; Tandem reactions ; Nitroalkanes ; Donor&ndash ; acceptor cyclopropanes
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：6 January 2016
• 年：2016
• 卷：57
• 期：1
• 页码：11-14
• 全文大小：894 K

文摘

The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C–C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)₂/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.