TY - JOUR
T1 - Copper-Mediated Cross-Dehydrogenative Coupling of 2-Methylpyridine and 8-Methylquinoline with Methyl Ketones and Benzamides
AU - Kumar, Gadde Sathish
AU - Boyle, Joshua William
AU - Tejo, Ciputra
AU - Chan, Philip Wai Hong
PY - 2016/2/4
Y1 - 2016/2/4
N2 - A synthetic method to prepare (E)-(pyridin-2-yl)enones and (E)-(quinolin-8-yl)enones that relies on the respective copper(I)-catalyzed formal cross-dehydrogenative coupling (CDC) reaction of 2-methylpyridine and 8-methylquinoline with methyl ketones has been discovered. The mechanism was delineated to follow a pathway involving oxidation of the N-heterocycle to its corresponding aldehyde adduct prior to reaction with the methyl ketone. The versatility and substrate dependent divergence in the reactivity of the copper-mediated CDC strategy was exemplified by its application to the synthesis of N-(quinolin-8-ylmethyl)amide and N-(quinolin-8-ylmethyl)aniline adducts on switching the cross-coupling partner to benzamides or an aniline derivative.
AB - A synthetic method to prepare (E)-(pyridin-2-yl)enones and (E)-(quinolin-8-yl)enones that relies on the respective copper(I)-catalyzed formal cross-dehydrogenative coupling (CDC) reaction of 2-methylpyridine and 8-methylquinoline with methyl ketones has been discovered. The mechanism was delineated to follow a pathway involving oxidation of the N-heterocycle to its corresponding aldehyde adduct prior to reaction with the methyl ketone. The versatility and substrate dependent divergence in the reactivity of the copper-mediated CDC strategy was exemplified by its application to the synthesis of N-(quinolin-8-ylmethyl)amide and N-(quinolin-8-ylmethyl)aniline adducts on switching the cross-coupling partner to benzamides or an aniline derivative.
KW - C-H bond activation
KW - copper
KW - cross-dehydrogenative coupling
KW - homogeneous catalysis
KW - synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=84949969600&partnerID=8YFLogxK
U2 - 10.1002/asia.201501096
DO - 10.1002/asia.201501096
M3 - Article
AN - SCOPUS:84949969600
SN - 1861-4728
VL - 11
SP - 385
EP - 389
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
IS - 3
ER -