PhI(OCOCF3)2-Mediated Construction of a 2-Spiropseudoindoxyl Skeleton via Cascade Annulation of 2-Sulfonamido-N-phenylpropiolamide Derivatives

作者：Zhang, Bobo; Zhang, Xiang; Hu, Bei; Sun, Desong; Wang, Senlin; Zhang-Negrerie, Daisy; Du, Yunfei^*

来源：Organic Letters, 2017, 19(4): 902-905.

DOI：10.1021/acs.orglett.7b00058

• METAL-FREE CONDITIONS
• MEDIATED OXIDATIVE CYCLIZATION
• HYPERVALENT IODINE CHEMISTRY
• DOMINO-REACTIONS
• POLYVALENT IODINE
• ORGANIC-SYNTHESIS
• SYNTHETIC APPLICATIONS
• SPIRO-PSEUDOINDOXYL
• NITROALKYNE REDOX
• CATALYSIS

A cascade annulation of 2-sulfonamido-N-phenylpropiolamide derivatives leading to the construction of the 2-spiropseudoindoxyl skeleton was realized under mild conditions with phenyliodine(III) bis(trifluoroacetate) (PIFA) as the sole oxidant. This metal-free spirocyclization process is suggested to encompass a sequential C(sp(2))-C(sp) and C(sp(2))-N bond formation with the concomitant introduction of a carbonyl oxygen.

• 出版日期2017-2-17
• 单位天津大学