Chinese Journal of Organic Chemistry >
Sodiump-Toluenesulfinate/KI-Mediated Aerobic Oxidative Iodination of Terminal Alkynes for Synthesis of 1-Iodoalkynes and 1,3-Diynes
Received date: 2020-07-09
Revised date: 2020-09-11
Online published: 2020-10-12
Supported by
the National Natural Science Foundation of China(21602035); the Natural Science Foundation of Guangdong Province(2016A030307030); the Program for Innovative Research Team of Guangdong University of Petrochemical Technology(519124)
A practical and environmentally friendly protocol for the synthesis of 1-iodoalkynes was developed via sodium sulfinate-KI mediated aerobic oxidative iodination of terminal alkynes. This transformation features simple operation, high efficiency, broad functional-group tolerance and mild reaction conditions. Especially, dioxygen was used in these reactions which avoided the addition of hazardous or toxic oxidants. Moreover, for the purpose of increasing the synthetic utility of this method, an efficient transition-metal-free synthetic approach to symmetrical 1,3-diynes was developed via the iodination/ homocoupling of terminal alkynes in a one-pot manner.
Key words： terminal alkyne; 1-iodoalkyne; air; sodium sulfinate; 1,3-diyne
Peng Zhou , Shangwei Feng , Huihua Qiu , Jiantao Zhang . Sodiump-Toluenesulfinate/KI-Mediated Aerobic Oxidative Iodination of Terminal Alkynes for Synthesis of 1-Iodoalkynes and 1,3-Diynes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 394 -399 . DOI: 10.6023/cjoc202007031
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