Synthesis of I(III)/S(VI) reagents and their reactivity in photochemical cycloaddition reactions with unsaturated bonds

The 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-su...

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Bibliographic Details
Published in:Nature communications 2022-11, Vol.13 (1), p.6588-6588, Article 6588
Main Authors: Li, Li, Deng, Kun, Xing, Yajie, Ma, Cheng, Ni, Shao-Fei, Wang, Zhaofeng, Huang, Yong
Format: Article
Language:English
Subjects:
639/638/403/933
639/638/403/934
Alkenes
Alkynes
Catalysis
Chemical reactions
Chemical synthesis
Cyanide
Cycloaddition
Electron transfer
Functional groups
Humanities and Social Sciences
Iodine
multidisciplinary
Nitriles
Organic chemistry
Photochemical reactions
Photochemicals
Reagents
Science
Science (multidisciplinary)
Single electrons
Structure-function relationships
Transition metals
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Summary:The 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. Novel methodologies for introducing sulfoxonium groups into organic molecules are desirable. Here the authors report the synthesis of an iodonium-sulfoxonium ylide reagent that enables the preparation of sulfoxonium-containing cyclic structures upon reaction with alkenes, alkynes, nitriles or allenes.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-022-34401-7