CFSONa-Mediated Five-Component Carbonylation of Triarylboroxines with TMSCF and THF/LiOH/NaI to Give Aroyloxyalkyl Iodides.

J Org Chem

State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, PR China.

Published: August 2022

Herein, we developed an efficient and transition-metal-free multicomponent coupling reaction for the synthesis of aroyloxyl alkyl iodides. In the reaction among 2,4,6-triarylboroxines, THF, TMSCF, LiOH, and NaI, five-component reactions could be precisely controlled by modulating CFSONa, supplying one type of aroyloxyl alkyl iodides in moderate to high yields. The reaction exhibits good functional group tolerance and a wide substrate scope and can be easily transformed into other useful compounds. The mechanism is proposed on the basis of the control experiments.

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http://dx.doi.org/10.1021/acs.joc.2c00662DOI Listing

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CFSONa-Mediated Five-Component Carbonylation of Triarylboroxines with TMSCF and THF/LiOH/NaI to Give Aroyloxyalkyl Iodides.

J Org Chem

August 2022

State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, PR China.

Herein, we developed an efficient and transition-metal-free multicomponent coupling reaction for the synthesis of aroyloxyl alkyl iodides. In the reaction among 2,4,6-triarylboroxines, THF, TMSCF, LiOH, and NaI, five-component reactions could be precisely controlled by modulating CFSONa, supplying one type of aroyloxyl alkyl iodides in moderate to high yields. The reaction exhibits good functional group tolerance and a wide substrate scope and can be easily transformed into other useful compounds.

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