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

doi:10.1021/om500408h

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 Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

21 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 language	English
Pages (from-to)	3500-3507
Number of pages	8
Journal	Organometallics
Volume	33
Issue number	13
DOIs	https://doi.org/10.1021/om500408h
Publication status	Published - Jul 14 2014

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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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. / Li, Jing; Noyori, Shintaro; Nakajima, Kiyohiko et al.
In: Organometallics, Vol. 33, No. 13, 14.07.2014, p. 3500-3507.

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Li, Jing

AU - Noyori, Shintaro

AU - Nakajima, Kiyohiko

AU - Nishihara, Yasushi

PY - 2014/7/14

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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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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

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