101-82-6Relevant articles and documents
LIGAND COUPLING REACTION ON THE PHOSPHORUS ATOM
Uchida, Yuzuru,Onoue, Katsumi,Tada, Nobuaki,Nagao, Fumio
, p. 567 - 570 (1989)
Phosphine oxides bearing two or three 2-pyridyl groups were found to react with organometallic compounds affording 2,2'-bipyridyl, 2-substituted pyridines and pyridine in substantial yields.Both ligand exchange and ligand coupling appear to take place within the penta-coordinated phosphorus intermediates formed incipiently.
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Hansen Jr.et al.
, p. 213,216 (1974)
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A novel iodide-catalyzed reduction of nitroarenes and aryl ketones with H3PO2 or H3PO3: Its application to the synthesis of a potential anticancer agent
Wu, George G.,Chen, Frank X.,LaFrance, Danny,Liu, Zhijian,Greene, Scott G.,Wong, Yee-Shing,Xie, Ji
, p. 5220 - 5223 (2011)
A novel iodide-catalyzed reduction method using hypophosphorous and/or phosphorus acids was developed to reduce both diaryl ketones and nitroarenes chemoselectively in the presence of chloro and bromo substituents in high yield. This efficient and practical method has been successfully applied to a large scale production of a potential anticancer agent
Palladium-catalyzed coupling reactions of (ArCH2)Ti(O-i-Pr) 3 with aromatic or heteroaromatic bromides
Chang, Shu-Ting,Li, Qinghan,Chiang, Ruei-Tang,Gau, Han-Mou
, p. 3956 - 3962 (2012)
Three benzyltitanium compounds of (ArCH2)Ti(O-i-Pr)3 (Ar = Ph (1a), 4-MeOC6H4 (1b), 4-FC6H 4 (1c)) were prepared and used as benzyl nucleophiles for coupling reactions with aromatic or heteroaromatic bromides. The simple catalytic system of 1 mol % Pd(OAc)2 and 2 mol % PCy3 worked efficiently for a wide variety of aromatic bromides, producing diarylmethanes in good to excellent yields of up to 96%. Coupling reactions of hindered aromatic bromides or aromatic bromides containing electron-withdrawing substituents were slower over longer reaction times of 3-6 h. Reactions of heteroaromatic bromides of bromopyridines, bromofurans, or bromothiophenes with benzyl reagents of 1a or 1b required either longer reaction times of 12-24 h or a higher reaction temperature of 80 °C, producing pyridyl-, furyl-, and thienyl-arylmethanes in moderate yields.
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Szmant,Harmuth
, p. 2909,2910,2911 (1964)
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Palladium-catalyzed regioselective benzylation-annulation of pyridine N -oxides with toluene derivatives via multiple c-h bond activations: Benzylation versus arylation
Kianmehr, Ebrahim,Faghih, Nasser,Khan, Khalid Mohammed
, p. 414 - 417 (2015)
A palladium-catalyzed cross-dehydrogenative coupling (CDC) reaction of pyridine N-oxides with toluenes has been developed that operates under mild conditions. 2-Benzylpyridines can be obtained directly by this method via a CDC reaction between unactivated toluenes and pyridine N-oxides. In addition, azafluorene N-oxides, of value for future medicinal chemistry applications, can be obtained successfully by this procedure via four tandem C-H bond activations.
Catalytic Selective Metal-Free Cross-Coupling of Heteroaromatic N-Oxides with Organosilanes
Puthanveedu, Mahesh,Polychronidou, Vasiliki,Antonchick, Andrey P.
supporting information, p. 3407 - 3411 (2019/05/10)
A metal-free, regioselective C-H functionalization of heteroaromatic N-oxides has been developed. The method enables the synthesis of various benzylated and alkynylated N-heterocycles in a transition-metal-free manner employing organosilanes as coupling partners. The unanticipated reactivity has been exploited for the synthesis of a number of symmetrical disubstituted acetylenes from ethynyltrimethylsilane via carbon-silicon bond metathesis.
Copper-Catalyzed Base-Controlled Diastereoselective Synthesis of Tetraarylethanes from 2-Benzylpyridines
Chandrasekar, Selvaraj,Karthikeyan, Iyyanar,Sekar, Govindasamy
, p. 1275 - 1283 (2017/12/26)
A highly efficient and base-controlled diastereoselective synthesis of tetraarylethanes through copper-catalyzed dehydrogenative homocoupling of readily available 2-benzylpyridines is reported. Various dl - and meso -tetraarylethanes were diastereoseletively synthesized by this new protocol, where base plays the role of the principle modulator: Grignard reagents selectively provide the C2 isomers, whereas KO t -Bu promotes the formation of the meso -tetraarylethanes. Interestingly, the presence of excess KO t -Bu generates the (E)-tetraarylethenes as the only product.
