An improved procedure for the preparation of Ru(bpz)3(PF6)2 via a high-yielding synthesis of 2,2’-bipyrazine

Schultz, Danielle M.; Sawicki, James W.

doi:10.3762/bjoc.11.9

Cited by 19 publications

(12 citation statements)

References 36 publications

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“…(E)-tert-butyldimethyl(4-(prop-1-en-1-yl)phenoxy)silane and 1-acetoxy-4-propenylbenzene were synthesized from trans-anethol (1) in two steps. Ru(bpz) 3 (PF 6 ) 2 was synthesized according to reported procedure 45 . Proton nuclear magnetic resonance ( 1 H-NMR) spectra were collected on 600 or 400 MHz NMR spectrometers using the deuterated solvent as an internal deuterium reference.…”

Section: Methodsmentioning

confidence: 99%

Interplay of arene radical cations with anions and fluorinated alcohols in hole catalysis

et al. 2019

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Chemical reactions via radical cation intermediates are of great interest in photoredox catalysis and electrosynthesis, while their reactivities are not clearly understood. For example, how the counter anions correlate with the reactivity of radical cations is still ambiguous. Here we report the effect of anions and fluorinated alcohols on the reactivity of organic radical cations in hole catalysis. The addition of salts in a radical cation Diels-Alder reaction under photoredox catalysis demonstrates that common anions significantly decease the efficiency of hole catalysis. The use of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) restores the reaction efficiency in the presence of salts, presumably due to solvation of the anions by HFIP to reduce their nucleophilicity. These findings enable hole catalysis under electrolytic conditions with greatly improved efficiency. The effect of anions and fluorinated alcohol described in this paper gives important insights on the fundamental understanding for the reactivity of arene radical cations.

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Section: Methodsmentioning

confidence: 99%

Interplay of arene radical cations with anions and fluorinated alcohols in hole catalysis

et al. 2019

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“…CO 2 and H 2 gases were purchased from Taiyo Nippon Sanso Corporation. [Rh(coe) 2 Cl] 2 (Van der Ent et al, 1990), P(4-CF 3 C 6 H 4 ) 3 (Suomalainen et al, 2001), Rh(PPh 3 ) 2 (OAc) ( 5 ) (Grushin et al, 1995), [Rh(cod)(OAc)] 2 (Chatt and Venanzi, 1957), Rh(PPh 3 ) 3 H ( 6 ) (Annibale and Song, 2014), [Ru(bpy) 3 ](PF 6 ) 2 (Damrauer et al, 1997), [Ru(dmbpy) 3 ](PF 6 ) 2 (Damrauer et al, 1997), [Ru(bpz) 3 ](PF 6 ) 2 (Schultz et al, 2015), Ir(ppy) 2 (dtbbpy)(PF 6 ) (Tellis et al, 2014), [Ir(dF(CF 3 )ppy) 2 (dtbbpy)](PF 6 ) (Slinker et al, 2004), fac -Ir(ppy) 3 (Tamayo et al, 2003), and diisopropylethylammonium acetate (Anouti et al, 2008) were prepared according to the published methods. 4-Cyanostyrene ( 1a ) was prepared by Wittig reaction of 4-cyanobenzaldehyde (Falk et al, 2013).…”

Section: Methodsmentioning

confidence: 99%

Improved Conditions for the Visible-Light Driven Hydrocarboxylation by Rh(I) and Photoredox Dual Catalysts Based on the Mechanistic Analyses

et al. 2019

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The improved catalytic conditions and detailed reaction mechanism of the visible-light driven hydrocarboxylation of alkenes with CO 2 by the Rh(I) and photoredox dual catalysts were investigated. The use of the benzimidazoline derivative, BI(OH)H, as a sacrificial electron donor was found to increase the yield of the hydrocarboxylated product by accelerating the reduction process. In addition, the incorporation of the cyclometalated Ir(III) complex as a second photosensitizer with [Ru(bpy) 3 ] 2+ photosensitizer also resulted in the promotion of the reduction process, supporting that the catalytic cycle includes two photochemical elementary processes: photoinduced electron and energy transfers.

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“…Reductive dimerization of 2-iodopyridine derivatives can be accomplished in the presence of Pd(OAc) 2 , with isopropanol serving as a reducing agent. 10 Interestingly, the water extract of pomegranate ash has also been successfully used as a terminal reductant in this pro-cess. 11 Furthermore, Pd(II) complexes immobilized on graphene oxide have proved to be active in the homocoupling of 2-chloropyridine, among a variety of other aromatic chlorides.…”

Section: Scheme 1 Ullmann Coupling Using Cu Bronzementioning

confidence: 99%

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

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Malkov

2021

Synthesis

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The sustained interest in the synthesis of new analogues of 2,2′-bipyridines is supported by the importance of compounds featuring bipyridine core in diverse areas of chemical, biomedical and materials research, which is relayed into the development of new approaches and the expansion of existing synthetic methods. This short review covers advances in the synthesis of 2,2′-bipyridines, including both the synthesis of compounds with a given substitution pattern and the development of new methods for assembling the bipyridine core. Special attention is directed toward the use of pyridine N-oxides and metal-free protocols to facilitate the formation of bipyridines. This short review focuses primarily on reports published in the last 5–6 years.1 Introduction2 Ullmann-Type Homocoupling Reactions3 Cross-Coupling Reactions in the Synthesis of Bipyridines4 Coupling Reactions Employing Pyridine N-Oxides5 Other Methods for the Synthesis of 2,2′-Bipyridines6 Conclusions and Outlook

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An improved procedure for the preparation of Ru(bpz)₃(PF₆)₂ via a high-yielding synthesis of 2,2’-bipyrazine

Cited by 19 publications

References 36 publications

Interplay of arene radical cations with anions and fluorinated alcohols in hole catalysis

Interplay of arene radical cations with anions and fluorinated alcohols in hole catalysis

Improved Conditions for the Visible-Light Driven Hydrocarboxylation by Rh(I) and Photoredox Dual Catalysts Based on the Mechanistic Analyses

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

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