Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of α-Oxygenated Ketones from Terminal Aryl Alkynes

Bao-Yi Ren, Bao-Yi Ren, Daokun Zhong, Nan Guo, Weikun Duan, Shuai Song, Xue Yang, Daokun Zhong, Nan Guo, Weikun Duan, Shuai Song, Xue Yang
2016 General Chemistry  
A facile and efficient method for preparation of α-oxygenated ketones has been developed via the reaction of terminal aryl alkynes with various iodobenzene dicarboxylates. When bis(trifluoroacetoxy)iodobenzene (PIFA) was used, α-hydroxy ketones were obtained in high to excellent yields. The hypervalent iodine(III) reagents can function as an electrophile, transferrable O-nucleophile, and an excellent leaving group. The protocol represents a direct, atom-efficient and metal-free conversion of
more » ... ynes into α-oxygenated ketones under mild conditions.
doi:10.21127/yaoyigc20150018 fatcat:ncewagzkcvfhxe3eidih5kodom