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
DOI:
10.1038/s44160-024-00595-5
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.
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.
