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Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent
Author(s) -
Zhang Xinglu,
Liu Zhiqiang,
Gao Yu,
Li Feng,
Tian Yaming,
Li Chunju,
Jia Xueshun,
Li Jian
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700953
Subject(s) - chemistry , synthon , peroxide , isocyanide , catalysis , reagent , reactivity (psychology) , coupling reaction , oxidative coupling of methane , radical , photochemistry , combinatorial chemistry , aryl , organic chemistry , medicine , alternative medicine , pathology , alkyl
A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N‐arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C−C and C−O bond‐forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used.