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Synfacts 2024; 20(11): 1143
DOI: 10.1055/s-0043-1773595
Synthesis of Materials and Unnatural Products

When Cycloaddition Met Mechanochemistry

Rezensent(en):
Dahui Zhao
,
Xudong Bai
Zhang X, Li D, Tan CC. H, Hanindita F, Hamamoto Y, Foster AS, *, Kawai S, *, Ito S. * Aalto University, Espoo, Finland; University of Tsukuba and Kanazawa University, Japan; Nanyang Technological University, Singapore
Synthesis of Azahexabenzocoronenium Salts through a Formal [3 + 3] Cycloaddition Strategy.

Nat. Synth. 2024;
3: 1283-1291
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Key words

azahexabenzocoro­nenium - cationic N-hetero­aromatics - formal [3+3] cycloaddition - reductive cyclization

Significance

A formal [3+3] cycloaddition is realized by reacting aromatic azomethine ylides with cyclopropenes, to produce a pyridinum ring. One of the products finally leads to a cationic N-embedded hexabenzocoronenium scaffold.


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Comment

Following a 1,3-dipolar cycloaddition and then oxidative rearrangement of azabicyclohexane into a pyridium ring, the dehydrogenative cyclization, which failed under the Scholl reaction conditions, is accomplished via a reductive mechanochemical (ball milling) process.


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Publikationsverlauf

Artikel online veröffentlicht:
16. Oktober 2024

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