27299-31-6Relevant academic research and scientific papers
Copper-catalysed, diboron-mediated: Cis -dideuterated semihydrogenation of alkynes with heavy water
Han, Xiaowei,Hu, Jiefeng,Chen, Cheng,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 6922 - 6925 (2019/06/18)
Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.
Cobalt-Catalyzed Ligand-Controlled Regioselective Hydroboration/Cyclization of 1,6-Enynes
Xi, Tuo,Lu, Zhan
, p. 1181 - 1185 (2017/08/09)
A ligand-controlled cobalt-catalyzed regioselective hydroboration/cyclization of 1,6-enynes with HBPin was developed by switching the size of the coordinated side arm to afford alkenylboronates and alkylboronates, respectively. Gram-scale reactions could be easily conducted, which is beneficial for further derivatizations. A primary mechanism was proposed on the basis of substrate-controlled experiments and deuterium experiments.
Deoxygenation of Unhindered Alcohols via Reductive Dealkylation of Derived Phosphate Esters
Chowdhury, Sarwat,Standaert, Robert F.
, p. 9957 - 9963 (2016/11/02)
Primary alcohols can be deoxygenated cleanly and in yields of 60-95% by reduction of derived diphenyl phosphate esters with lithium triethylborohydride in tetrahydrofuran at room temperature. Selective deoxygenation of a primary alcohol in the presence of a secondary alcohol was demonstrated. The two-step process can be performed in one pot, making it simple and convenient.
Catalytic Semireduction of Internal Alkynes with All-Metal Aromatic Complexes
Deyris, Pierre-Alexandre,Ca?eque, Tatiana,Wang, Yanlan,Retailleau, Pascal,Bigi, Franca,Maggi, Raimondo,Maestri, Giovanni,Malacria, Max
, p. 3266 - 3269 (2015/10/28)
A simple catalytic method involving all-metal aromatic frameworks as precatalysts ensures an efficient route to (Z)-alkenes. Aromatic triangular palladium clusters were used to reduce internal alkynes without any trace of the formation of alkane side products. These trinuclear complexes provide a catalytic system that parallels the activity and selectivity of their best mononuclear peers, and the catalyst likely operates through complementary mechanisms.
Encapsulated molecular catalysts in polysiloxane gels: Ruthenium cluster-catalyzed isomerization of alkenes
Motoyama, Yukihiro,Abe, Motonori,Kamo, Kazuyuki,Kosako, Yusuke,Nagashima, Hideo
supporting information; experimental part, p. 5321 - 5323 (2009/03/11)
Novel ruthenium-encapsulating polysiloxane gels are prepared by treatment of polymethylhydrosiloxane with diols in the presence of (μ3, η2,η3,η5-acenaphthylene)Ru 3(CO)7, and act as reusable catalysts in the isomerization of alkenes without leakage of the catalyst species. The Royal Society of Chemistry.
Chemoselective removal of allylic formyloxy group using SmI2
Shibuya,Shiratsuchi
, p. 431 - 449 (2007/10/02)
A variety of allylic formates are chemoselectively transformed into th corresponding olefins in excellent yields on treatment with SmI2 in THF-HMPA-H2O (20:5:1), even though allylic acetate and allylic ether groups are present in the same molecule.
