99329-30-3Relevant articles and documents
Pd-PEPPSI: Water-Assisted Suzuki?Miyaura Cross-Coupling of Aryl Esters at Room Temperature using a Practical Palladium-NHC (NHC=N-Heterocyclic Carbene) Precatalyst
Li, Guangchen,Shi, Shicheng,Lei, Peng,Szostak, Michal
, p. 1538 - 1543 (2018)
A Pd-PEPPSI-catalyzed (Pd=Palladium, PEPPSI=pyridine-enhanced precatalyst preparation stabilization and initiation) Suzuki-Miyaura cross-coupling of aryl esters via selective C?O cleavage at room temperature is reported. The developed catalyst system displays broad substrate scope with respect to both components under practical ambient reaction conditions using readily-available, cheap, modular, air- and moisture-stable Pd-NHC precatalyst (NHC=N-heterocyclic carbene). The use of water proved crucial for achieving high reactivity in this coupling. The catalyst system represents the mildest conditions for the Suzuki?Miyaura cross-coupling of aryl esters reported to date. The protocol also allowed for achieving TON >1,000 (TON=turnover number) in the Suzuki?Miyaura ester coupling for the first time. (Figure presented.).
General Method for the Suzuki-Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature
Lei, Peng,Meng, Guangrong,Ling, Yun,An, Jie,Nolan, Steven P.,Szostak, Michal
, p. 6510 - 6513 (2017/12/26)
A general, highly selective method for the room temperature Suzuki-Miyaura cross-coupling of commonly encountered primary benzamides is reported. A combination of site-selective N,N-di-Boc-activation (tert-butoxycarbonyl activation) of the amide nitrogen with practical air- and moisture-stable, well-defined, and highly reactive [Pd(NHC)(cin)Cl] (NHC = N-heterocyclic carbene; cin = cinnamyl) provides a highly effective route to biaryl ketones from primary amides in high yields. For the first time, a TON of >1000 has been achieved in amide acyl cross-coupling.
One-pot synthesis of heteroaryl and diheteroaryl ketones through palladium-catalyzed 1,2-addition and oxidation
Kuriyama, Masami,Hamaguchi, Norihisa,Sakata, Keisuke,Onomura, Osamu
, p. 3378 - 3385 (2013/06/27)
A synthetic method was developed for the preparation of heteroaryl and diheteroaryl ketones from aldehydes and organoboronic acids through a palladium-catalyzed 1,2-addition and oxidation that uses an aryl iodide as the oxidant. This one-pot process shows high tolerance for a broad range of heterocyclic substrates by using 1.0-3.0 mol-% of the catalyst that is formed from allylpalladium chloride dimer and a thioether-imidazolinium chloride. In addition to fine-tuning the catalytic system, the use of a sterically hindered aryl iodide that has a substituent at the ortho position, such as 2-iodotoluene, is important to obtain the desired ketones with heterocyclic moieties in good to excellent yields. The one-pot synthesis of heteroaryl and diheteroaryl ketones was achieved by a palladium-catalyzed 1,2-addition and oxidation. This catalytic process with 1.0-3.0 mol-% catalyst loading tolerates a broad range of heterocyclic substrates to give ketones with heterocyclic moieties in good to excellent yields. Copyright
