TY - JOUR
T1 - One-Pot Cross-Coupling/C-H Functionalization Reactions
T2 - Quinoline as a Substrate and Ligand through N-Pd Interaction
AU - Shanahan, Rachel M.
AU - Hickey, Aobha
AU - Bateman, Lorraine M.
AU - Light, Mark E.
AU - McGlacken, Gerard P.
N1 - Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/2/21
Y1 - 2020/2/21
N2 - Herein, we report a one-pot process that marries mechanistically distinct, traditional cross-coupling reactions with C-H functionalization using the same precatalyst. The reactions proceed in yields of up to 95%, in air, and require no extraneous ligand. The reactions are thought to be facilitated by harnessing the substrate quinoline as an N-ligand, and evidence of the palladium-quinoline interaction is provided by 1H-15N HMBC NMR spectroscopy and X-ray crystallographic structures. Application of the methodology is demonstrated by the quick formation of fluorescent, I -extended frameworks.
AB - Herein, we report a one-pot process that marries mechanistically distinct, traditional cross-coupling reactions with C-H functionalization using the same precatalyst. The reactions proceed in yields of up to 95%, in air, and require no extraneous ligand. The reactions are thought to be facilitated by harnessing the substrate quinoline as an N-ligand, and evidence of the palladium-quinoline interaction is provided by 1H-15N HMBC NMR spectroscopy and X-ray crystallographic structures. Application of the methodology is demonstrated by the quick formation of fluorescent, I -extended frameworks.
UR - https://www.scopus.com/pages/publications/85080851477
U2 - 10.1021/acs.joc.9b03321
DO - 10.1021/acs.joc.9b03321
M3 - Article
C2 - 31971802
AN - SCOPUS:85080851477
SN - 0022-3263
VL - 85
SP - 2585
EP - 2596
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -