111991-14-1Relevant articles and documents
Practical iron-catalyzed hydrogen peroxide epoxidation of aromatic olefins using a combination of two kinds of simple picolinate ligands under halide-free reaction conditions
Chishiro, Takefumi,Kon, Yoshihiro,Nakashima, Takuya,Goto, Midori,Sato, Kazuhiko
, p. 623 - 627 (2014)
High-yield syntheses of epoxides using an iron complex having two types of picolinates in the presence of hydrogen peroxide under halide-free reaction conditions were achieved. The reaction is very simple. The complex, prepared with iron(II) acetate, 2-pi
Highly enantioselective bioinspired epoxidation of electron-deficient olefins with H2O2 on aminopyridine mn catalysts
Ottenbacher, Roman V.,Samsonenko, Denis G.,Talsi, Evgenii P.,Bryliakov, Konstantin P.
, p. 1599 - 1606 (2014)
The asymmetric epoxidation of various electron-deficient olefins with H2O2 in the presence of a novel family of chiral bioinspired bipyrrolidine-derived aminopyridine manganese(II) complexes [LM II(OTf)2] is rep
Regioselective hydrosilylation of epoxides catalysed by nickel(II) hydrido complexes
Wenz, Jan,Wadepohl, Hubert,Gade, Lutz H.
, p. 4308 - 4311 (2017)
Bench-stable nickel fluoride complexes bearing NNN pincer ligands have been employed as precursors for the regioselective hydrosilylation of epoxides at room temperature. A nickel hydride assisted epoxide opening is followed by the cleavage of the newly formed nickel oxygen bond by σ-bond metathesis with a silane.
Effect of the Ligand Backbone on the Reactivity and Mechanistic Paradigm of Non-Heme Iron(IV)-Oxo during Olefin Epoxidation
Biswas, Jyoti Prasad,Ansari, Mursaleem,Paik, Aniruddha,Sasmal, Sheuli,Paul, Sabarni,Rana, Sujoy,Rajaraman, Gopalan,Maiti, Debabrata
supporting information, p. 14030 - 14039 (2021/05/11)
The oxygen atom transfer (OAT) reactivity of the non-heme [FeIV(2PyN2Q)(O)]2+ (2) containing the sterically bulky quinoline-pyridine pentadentate ligand (2PyN2Q) has been thoroughly studied with different olefins. The ferryl-oxo complex 2 shows excellent OAT reactivity during epoxidations. The steric encumbrance and electronic effect of the ligand influence the mechanistic shuttle between OAT pathway I and isomerization pathway II (during the reaction stereo pure olefins), resulting in a mixture of cis-trans epoxide products. In contrast, the sterically less hindered and electronically different [FeIV(N4Py)(O)]2+ (1) provides only cis-stilbene epoxide. A Hammett study suggests the role of dominant inductive electronic along with minor resonance effect during electron transfer from olefin to 2 in the rate-limiting step. Additionally, a computational study supports the involvement of stepwise pathways during olefin epoxidation. The ferryl bend due to the bulkier ligand incorporation leads to destabilization of both (Formula presented.) and (Formula presented.) orbitals, leading to a very small quintet–triplet gap and enhanced reactivity for 2 compared to 1. Thus, the present study unveils the role of steric and electronic effects of the ligand towards mechanistic modification during olefin epoxidation.
MeOTf/KI-catalyzed efficient synthesis of 2-arylnaphthalenesviacyclodimerization of styrene oxides
Chen, Chao,Xi, Chanjuan,Zhang, Zeyu,Zou, Song
supporting information, p. 8559 - 8565 (2021/10/20)
The MeOTf/KI-catalyzed synthesis of 2-arylnaphthalene derivatives from aryl ethylene oxides in alcohol under ambient conditions is described. The present protocol has a higher atom efficiency and wider substrate applicability with excellent yields. The reaction proceeded using the aryl ethylene oxides to give 2-arylnaphthalenes either in homo-coupling or in cross-coupling. The reaction could also be carried out at the gram scale in minutes.
