1207290-13-8Relevant articles and documents
N-Iodosuccinimide-Mediated Dimerization of 2-Alkynylnaphthols: A Highly Diastereoselective Construction of Bridged Polycyclic Compounds via Vinylidene ortho-Quinone Methide Intermediate
Tan, Yu,Zhao, Zhengxing,Chen, Zhili,Huang, Shengli,Jia, Shiqi,Peng, Lei,Xu, Da,Qin, Wenling,Yan, Hailong
supporting information, p. 4461 - 4466 (2020/06/03)
An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good to excellent yields. The reaction proceeded under mild conditions using N-iodosuccinimide as a promoter, simultaneously constructing one new C-O bond and two new C-C bonds. A tetra-substituted vinylidene ortho-quinone methide intermediate was likely involved, and the steric hindrance of substituents played a critical role in this transformation.
Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines
Yuan, Zheliang,Cheng, Ran,Chen, Pinhong,Liu, Guosheng,Liang, Steven H.
supporting information, p. 11882 - 11886 (2016/11/17)
Iodonium compounds play a pivotal role in18F-fluorination of radiopharmaceuticals containing non-activated arenes. However, preparation of these species is limited to oxidation conditions or exchange with organometallics that are prepared from aryl halides. Herein we describe a novel “one-pot” process to assemble aryl(isoquinoline)iodonium salts in 40–94 % yields from mesoionic carbene silver complex and Aryl-I-Py2(OTf)2. The method is general, practical, and compatible with well-functionalized molecules as well as useful for the preparation of a wide range of18F-labeled isoquinolines resulting in up to 92 % radiochemical conversion. As proof of concept, a fluorinated isoquinoline alkaloid,18F-aspergillitine is prepared in 10 % isolated radiochemical yield from the corresponding phenyl(aspergillitine)iodonium salt.