Vicinal Difluoroalkylation and Aminosulfonylation of Alkynes under Photoinduced Conditions

A photoinduced vicinal difluoroalkylation and aminosulfonylation of alkynes under photocatalysis was realized. The combination of ethyl 2‐bromo‐2,2‐difluoroacetate, alkynes, and DABCO⋅(SO2)2 with hydrazines, catalyzed by 9‐mes‐10‐methyl acridinium perchlorate in the presence of visible light, afford...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-01, Vol.23 (5), p.1032-1035
Main Authors: Xiang, Yuanchao, Li, Yuewen, Kuang, Yunyan, Wu, Jie
Format: Article
Language:English
Subjects:
alkyne
Alkynes
aminosulfonylation
Chemistry
difluoroalkylation
Hydrazines
Insertion
Perchlorates
Photocatalysis
Radicals
Stereoselectivity
Sulfur dioxide
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Summary:A photoinduced vicinal difluoroalkylation and aminosulfonylation of alkynes under photocatalysis was realized. The combination of ethyl 2‐bromo‐2,2‐difluoroacetate, alkynes, and DABCO⋅(SO2)2 with hydrazines, catalyzed by 9‐mes‐10‐methyl acridinium perchlorate in the presence of visible light, afforded (E)‐ethyl 2,2‐difluoro‐4‐aryl‐4‐sulfamoylbut‐3‐enoates in good yields with high stereoselectivity. This four‐component reaction proceeds through radical addition with the insertion of sulfur dioxide. Photocatalyzed tandem reaction: Photoinduced vicinal difluoroalkylation and aminosulfonylation of alkynes was realized. Combination of ethyl 2‐bromo‐2,2‐difluoroacetate, alkynes, and DABCO⋅ (SO2)2 with hydrazines, catalyzed by 9‐mes‐10‐methyl acridinium perchlorate in the presence of visible light, afforded (E)‐ethyl 2,2‐difluoro‐4‐aryl‐4‐sulfamoylbut‐3‐enoates in good yields with high stereoselectivity. This four‐component reaction proceeds through radical addition with the insertion of sulfur dioxide.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201605336