Open AccessRegioselective Ru(II)/Pd(0) Dual Catalysis: One-Pot C–H Diarylation of Five-Membered Heterocyclic Derivatives
Author(s) -
Hamad H. Al Mamari,
Uroš Grošelj,
Franc Požgan,
Helena Brodnik
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01983
Subject(s) - regioselectivity , azine , catalysis , chemistry , moiety , thiophene , furan , ruthenium , combinatorial chemistry , surface modification , medicinal chemistry , organic chemistry
Herein, we report a one-pot site-selective dual metal catalyzed C-H diarylation reaction for the synthesis of multiarylated thiophene and furan derivatives in yields up to 92%. The regioselectivity of the developed methodology was achieved with the sequential use of two metal catalysts within a single vessel, starting with a Ru(II)-catalyzed C3 arylation assisted by an azine directing group, followed by a Pd(0)-catalyzed C-H functionalization on the C5-position of the five-membered heterocycle. Furthermore, the kinetic studies support that the position of the nitrogen atom within the azine moiety exhibits an evident effect on the efficiency of the ruthenium-catalyzed arylation step.