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

doi:10.21127/yaoyigc20150018

General Chemistry ›› 2016, Vol. 2 ›› Issue (1): 49-54.DOI: 10.21127/yaoyigc20150018

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

Bao-Yi Ren,*^,a,b Daokun Zhong,^a Nan Guo,^a Weikun Duan,^a Shuai Song,^a Xue Yang^b

^a Key Laboratory of Inorganic Molecule-Based Chemistry of Liaoning Province, Shenyang University of Chemical Technology, Shenyang, Liaoning 110142, China
^b Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, China

Received:2015-12-22 Accepted:2016-01-15 Online:2016-03-31 Published:2016-03-31
Contact: Bao-Yi Ren

Abstract

Abstract:

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 alkynes into α-oxygenated ketones under mild conditions.

Key words: iodobenzene dicarboxylates, transferrable oxygen sources, #cod#x003B1;-oxygenated ketones

Bao-Yi Ren, Daokun Zhong, Nan Guo, Weikun Duan, Shuai Song, Xue Yang. Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of α-Oxygenated Ketones from Terminal Aryl Alkynes[J]. General Chemistry, 2016, 2(1): 49-54.

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

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