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Highly Efficient Suzuki–Miyaura Coupling of Aryl Tosylates and Mesylates Catalyzed by Stable, Cost‐Effective [1,3‐Bis(diphenylphosphino)propane]nickel(II) Chloride [Ni(dppp)Cl 2 ] with only 1 mol% Loading
Author(s) -
Gao Han,
Li You,
Zhou YiGuo,
Han FuShe,
Lin YingJie
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000710
Subject(s) - chemistry , aryl , nickel , steric effects , catalysis , chloride , combinatorial chemistry , ligand (biochemistry) , trifluoromethanesulfonate , propane , organic chemistry , biochemistry , alkyl , receptor
We present a highly active, inexpensive, universally applicable, and markedly stable [1,3‐bis(diphenylphosphino)propane]nickel(II) chloride [Ni(dppp)Cl 2 ] catalyst that is capable of effecting the Suzuki–Miyaura cross‐coupling of the inherently less reactive but readily available aryl tosylates and mesylates with only 1 mol% loading and in the absence of extra supporting ligand. Under the optimized reaction conditions, cross‐coupling of a wide range of activated, non‐activated, and deactivated, as well as sterically hindered and heteroaromatic substrates (36 examples) could proceed efficiently to afford the coupled products in 53–99% yields. Consequently, the results presented in this work provide a significant advance in Suzuki–Miyaura cross‐coupling in terms of generality, practicality, and cost which are key concerns in recent research regarding transition metal‐catalyzed cross‐couplings.