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Cu‐Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO
Author(s) -
Zhu Yamin,
Li Linyi,
Shen Zengming
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501823
Subject(s) - cyanation , acetonitrile , chemistry , moiety , catalysis , reagent , reactivity (psychology) , dual role , substrate (aquarium) , combinatorial chemistry , organic chemistry , medicinal chemistry , medicine , oceanography , alternative medicine , pathology , geology
Abstract The cyanation of arylboronic acids by using acetonitrile as the “CN” source has been achieved under a Cu(cat.)/TEMPO system (TEMPO=2,2,6,6‐tetramethylpiperidine N ‐oxide). The broad substrate scope includes a variety of electron‐rich and electron‐poor arylboronic acids, which react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPOCH 2 CN, generated in situ, is an active cyanating reagent, and shows high reactivity for the formation of the CN − moiety. Moreover, TEMPO acts as a cheap oxidant to enable the reaction to be catalytic in copper.