TY - JOUR
T1 - Regioselective Ru(II)/Pd(0) Dual Catalysis
T2 - One-Pot C-H Diarylation of Five-Membered Heterocyclic Derivatives
AU - Al Mamari, Hamad H.
AU - Grošelj, Uroš
AU - Požgan, Franc
AU - Brodnik, Helena
N1 - Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/2/19
Y1 - 2021/2/19
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.0c01983
DO - 10.1021/acs.joc.0c01983
M3 - Article
C2 - 33512169
AN - SCOPUS:85100858953
SN - 0022-3263
VL - 86
SP - 3138
EP - 3151
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -