RT Journal Article
SR Electronic
T1 Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine
JF Science Advances
JO Sci Adv
FD American Association for the Advancement of Science
SP e1500656
DO 10.1126/sciadv.1500656
VO 1
IS 9
A1 Wu, Kun
A1 Huang, Zhiliang
A1 Qi, Xiaotian
A1 Li, Yingzi
A1 Zhang, Guanghui
A1 Liu, Chao
A1 Yi, Hong
A1 Meng, Lingkui
A1 Bunel, Emilio E.
A1 Miller, Jeffrey T.
A1 Pao, Chih-Wen
A1 Lee, Jyh-Fu
A1 Lan, Yu
A1 Lei, Aiwen
YR 2015
UL http://advances.sciencemag.org/content/1/9/e1500656.abstract
AB Copper-catalyzed aerobic oxidative C–H/N–H coupling between simple ketones and diamines was developed toward the synthesis of a variety of pyrazines. Various substituted ketones were compatible for this transformation. Preliminary mechanistic investigations indicated that radical species were involved. X-ray absorption fine structure experiments elucidated that the Cu(II) species 5 coordinated by two N atoms at a distance of 2.04 Å and two O atoms at a shorter distance of 1.98 Å was a reactive one for this aerobic oxidative coupling reaction. Density functional theory calculations suggested that the intramolecular coupling of cationic radicals was favorable in this transformation.