Premium
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
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom