132682-77-0Relevant articles and documents
Nonsymmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling
Boyle, Benjamin T.,Hilton, Michael C.,McNally, Andrew
supporting information, p. 15441 - 15449 (2019/11/02)
Distinct approaches to synthesize bis-azine biaryls are in demand as these compounds have multiple applications in the chemical sciences and are challenging targets for metal-catalyzed cross-coupling reactions. Most approaches focus on developing new reagents as the formal nucleophilic coupling partner that can function in metal-catalyzed processes. We present an alternative approach using pyridine and diazine phosphines as nucleophilic partners and chloroazines where the heterobiaryl bond is formed via a tandem SNAr-phosphorus ligand-coupling sequence. The heteroaryl phosphines are prepared from chloroazines and are bench-stable solids. A range of bis-azine biaryls can be formed from abundant chloroazines using this strategy that would be challenging using traditional approaches. A one-pot cross-electrophile coupling of two chloroazines is feasible, and we also compared the phosphorus-mediated strategy with metal-catalyzed coupling reactions to show advantages and compatibility.
Highly chemoselective metal-free reduction of phosphine oxides to phosphines
Li, Yuehui,Lu, Liang-Qiu,Das, Shoubhik,Pisiewicz, Sabine,Junge, Kathrin,Beller, Matthias
, p. 18325 - 18329 (2013/01/15)
Unprecedented chemoselective reductions of phosphine oxides to phosphines proceed smoothly in the presence of catalytic amounts of specific Br?nsted acids. By utilizing inexpensive silanes, e.g., PMHS or (EtO)2MeSiH, other reducible functional groups such as ketones, aldehydes, olefins, nitriles, and esters are well-tolerated under optimized conditions.
General and selective copper-catalyzed reduction of tertiary and secondary phosphine oxides: Convenient synthesis of phosphines
Li, Yuehui,Das, Shoubhik,Zhou, Shaolin,Junge, Kathrin,Beller, Matthias
supporting information; experimental part, p. 9727 - 9732 (2012/07/14)
Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination domino sequence allows for the synthesis of a variety of functionalized aromatic and aliphatic phosphines in good yields.
