Skeletal Rearrangement of Cyano-Substituted Iminoisobenzofurans into Alkyl 2-Cyanobenzoates Catalyzed by B(C6F5)3

被引：7

作者：

Li, Jing ^{[1
]}

Okuda, Yasuhiro ^{[1
]}

Zhao, Jiaji ^{[1
]}

Mori, Seiji ^{[2
]}

Nishihara, Yasushi ^{[1
,3
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Earth Life & Mol Sci, Okayama 7008530, Japan

[2] Ibaraki Univ, Fac Sci, Mito, Ibaraki 3108512, Japan

[3] Japan Sci & Technol Agcy, ACT C, Kawaguchi, Saitama 3320012, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 19期

关键词：

GAUSSIAN-BASIS SETS; MOLECULAR CALCULATIONS; SELECTIVE HYDRATION; ARYL HALIDES; PALLADIUM; BOND; NITRILES; CYANOESTERIFICATION; CYANATION; ARYNES;

D O I：

10.1021/ol5026519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 a-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.

引用

页码：5220 / 5223

页数：4

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