Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3

Jing Li, Yasuhiro Okuda, Jiaji Zhao, Seiji Mori, Yasushi Nishihara

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate α-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.

Original languageEnglish
Pages (from-to)5220-5223
Number of pages4
JournalOrganic Letters
Volume16
Issue number19
DOIs
Publication statusPublished - Oct 3 2014

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Cyanides
cyanides
Discrete Fourier transforms
cleavage
thermodynamics
Benzoates
Thermodynamics
Byproducts
ions
Ions

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3. / Li, Jing; Okuda, Yasuhiro; Zhao, Jiaji; Mori, Seiji; Nishihara, Yasushi.

In: Organic Letters, Vol. 16, No. 19, 03.10.2014, p. 5220-5223.

Research output: Contribution to journalArticle

Li, Jing ; Okuda, Yasuhiro ; Zhao, Jiaji ; Mori, Seiji ; Nishihara, Yasushi. / Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3. In: Organic Letters. 2014 ; Vol. 16, No. 19. pp. 5220-5223.
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