New entry to the synthesis of α-iminonitriles by Lewis acid mediated isomerization of cyano-substituted iminoisobenzofurans prepared by palladium-catalyzed three-component coupling of arynes, isocyanides, and cyanoformates

Jing Li, Shintaro Noyori, Kiyohiko Nakajima, Yasushi Nishihara

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A variety of α-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)2(dppf)] (BF4)2 as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. α-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into α-iminonitriles was observed.

Original languageEnglish
Pages (from-to)3500-3507
Number of pages8
JournalOrganometallics
Volume33
Issue number13
DOIs
Publication statusPublished - Jul 14 2014

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Lewis Acids
Palladium
Cyanides
Isomerization
entry
isomerization
palladium
acids
Catalysts
synthesis
products
hydrides
catalysts
diisobutylaluminum

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

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title = "New entry to the synthesis of α-iminonitriles by Lewis acid mediated isomerization of cyano-substituted iminoisobenzofurans prepared by palladium-catalyzed three-component coupling of arynes, isocyanides, and cyanoformates",
abstract = "A variety of α-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)2(dppf)] (BF4)2 as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. α-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into α-iminonitriles was observed.",
author = "Jing Li and Shintaro Noyori and Kiyohiko Nakajima and Yasushi Nishihara",
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journal = "Organometallics",
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TY - JOUR

T1 - New entry to the synthesis of α-iminonitriles by Lewis acid mediated isomerization of cyano-substituted iminoisobenzofurans prepared by palladium-catalyzed three-component coupling of arynes, isocyanides, and cyanoformates

AU - Li, Jing

AU - Noyori, Shintaro

AU - Nakajima, Kiyohiko

AU - Nishihara, Yasushi

PY - 2014/7/14

Y1 - 2014/7/14

N2 - A variety of α-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)2(dppf)] (BF4)2 as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. α-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into α-iminonitriles was observed.

AB - A variety of α-iminonitriles were formed as the minor products of three-component coupling reactions of arynes, isocyanides, and cyanoformates in the presence of the cationic palladium complex [Pd(NCPh)2(dppf)] (BF4)2 as the catalyst, along with cyano-substituted iminoisobenzofurans as the major products. α-Iminonitriles obtained from this process are hardly accessible by conventional methods. In addition, when the isolated iminoisobenzofurans were treated with diisobutylaluminum hydride (DIBAL-H) or AlMe3, the transformation of cyano-substituted iminoisobenzofurans into α-iminonitriles was observed.

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