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 - Funding Information:
Dedicated to Prof. Pierre H. Dixneuf for his outstanding contribution to organometallic chemistry and ruthenium catalysis. Special thanks go to Maša Kastner, Tina Pečarič Strnad, and Urša Rozman for laboratory support. We thank the Slovenian Research Agency for financial support through grant P1-0179. We also acknowledge the Centre of Excellence EN-FIST.
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.
UR - http://www.scopus.com/inward/record.url?scp=85100858953&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85100858953&partnerID=8YFLogxK
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 -