Abstract
AbstractThe development of novel methodologies for the introduction of the sulfoxonium group under mild conditions is appealing but remains underexplored. Herein we report the synthesis of a class of hypervalent iodine reagents with a transferrable sulfoxonium group. These compounds enable mixed iodonium-sulfoxonium ylide reactivity. These well-defined reagents are examined in visible-light-promoted cyclization reactions with a wide range of unsaturated bonds including alkenes, alkynes, nitriles, and allenes. Two distinct cyclization pathways are identified, which are controlled by the substituent of the unsaturated bond. The cycloaddition protocol features simple operation, mild reaction conditions, and excellent functional group tolerance, affording a broad range of sulfoxonium-containing cyclic structures in moderate to excellent yields. Furthermore, the sufoxonium group in the product can be transformed into diverse functional groups and structural motifs via single electron transfer and transition-metal catalysis.
Funder
National Natural Science Foundation of China
Shenzhen Science and Technology Innovation Commission
Publisher
Springer Science and Business Media LLC
Subject
General Physics and Astronomy,General Biochemistry, Genetics and Molecular Biology,General Chemistry,Multidisciplinary
Cited by
6 articles.
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