733810-73-6Relevant articles and documents
Air-Stable Iron-Based Precatalysts for Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Aryl Boronic Esters
Wong, Alexander S.,Zhang, Bufan,Li, Bo,Neidig, Michael L.,Byers, Jeffery A.
, p. 2461 - 2472 (2021/11/01)
The development of an air-stable iron(III)-based precatalyst for the Suzuki-Miyaura cross-coupling reaction of alkyl halides and unactivated aryl boronic esters is reported. Despite benefits to cost and toxicity, the proclivity of iron(II)-based complexes to undergo deactivationviaoxidation or hydrolysis is a limiting factor for their widespread use in cross-coupling reactions compared to palladium-based or nickel-based complexes. The new octahedral iron(III) complex demonstrates long-term stability on the benchtop as assessed by a combination of1H NMR spectroscopy, M?ssbauer spectroscopy, and its sustained catalytic activity after exposure to air. The improved stability of the iron-based catalyst facilitates an improved protocol in which Suzuki-Miyaura cross-coupling reactions of valuable substrates can be assembled without the use of a glovebox and access a diverse scope of products similar to reactions assembled in the glovebox with iron(II)-based catalysts.
Rational Design of an Iron-Based Catalyst for Suzuki–Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles
Byers, Jeffery A.,Crockett, Michael P.,Li, Bo,Wong, Alexander S.
supporting information, p. 5392 - 5397 (2020/03/04)
Suzuki–Miyaura cross-coupling reactions between a variety of alkyl halides and unactivated aryl boronic esters using a rationally designed iron-based catalyst supported by β-diketiminate ligands are described. High catalyst activity resulted in a broad substrate scope that included tertiary alkyl halides and heteroaromatic boronic esters. Mechanistic experiments revealed that the iron-based catalyst benefited from the propensity for β-diketiminate ligands to support low-coordinate and highly reducing iron amide intermediates, which are very efficient for effecting the transmetalation step required for the Suzuki–Miyaura cross-coupling reaction.
Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis
Liu, Xu-Ge,Zhou, Chu-Jun,Lin,Han, Xiang-Lei,Zhang, Shang-Shi,Li, Qingjiang,Wang, Honggen
supporting information, p. 13096 - 13100 (2018/09/21)
A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.