Insertion of arynes into carbon-chlorine bonds of chlorotriazines

Chemistry Letters

Volumn 38, Issue 12, 2009, Pages 1132-1133

  Yoshida, Hiroto ^a   Mimura, Yasuhiro ^a   Ohshita, Joji ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449148718     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.1132     Document Type: Article

References (20)

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7. We have also reported on insertion reactions of arynes into other nucleophilic-electrophilic σ bonds: H. Yoshida, E. Shirakawa, Y. Honda, T. Hiyama, Angew. Chem., Int. Ed. 2002, 41, 3247;
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15. For a review on insertion reactions of arynes into element-element σ bonds, see: D. Peña, D. Pérez, E. Guitián, Angew. Chem., Int. Ed. 2006, 45, 3579.
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17. These products were isolated as hydroxytriazines probably via the hydrolysis of the unreacted carbon-chlorine bond.
18. The reaction of other nitrogen-heteroaromatic compounds including 2-chloropyridine, 2-bromopyridine, 2-bromo-3-nitropyridine, and 2-bromopyrimidine with benzyne did not afford the desired insertion products at all.
19. This result also indicates that the common pathway for the aryne insertion reactions into nucleophilic-electrophilic σ bonds, which starts with the formation of zwitterions, would not be operative in the present reaction. For the detailed pathway, see Refs. 3 and 4.
20. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.