443640-59-3Relevant academic research and scientific papers
Tetrahydroxydiboron-Promoted Radical Addition of Alkynols
Sun, Ze-Ying,Zhou, Sen,Yang, Kai,Guo, Minjie,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei
supporting information, p. 6214 - 6219 (2020/08/12)
Tetrahydroxydiboron has previously been used as a borylation or reducing reagent in organic synthesis. Herein, we present a novel tetrahydroxydiboron-promoted radical addition of internal alkynes followed by intramolecular oxidation of alcohol through 1,5-hydrogen atom transfer. Preliminary mechanistic studies showed that the process might be initiated through N,N-dimethylformamide-assisted homolytic cleavage of tetrahydroxydiboron. This process provides a convenient synthesis of fluoroalkyl-substituted alkenes with a pendant aldehyde or ketone moiety.
Novel highly potent OXE receptor antagonists with prolonged plasma lifetimes that are converted to active metabolites in vivo in monkeys
Ye, Qiuji,Chourey, Shishir,Reddy, Chintam Nagendra,Wang, Rui,Cossette, Chantal,Gravel, Sylvie,Slobodchikova, Irina,Vuckovic, Dajana,Rokach, Joshua,Powell, William S.
supporting information, p. 388 - 401 (2020/01/25)
Background and Purpose: The 5-lipoxygenase product 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE), acting through the OXE receptor, is a potent eosinophil chemoattractant that may be an important proinflammatory mediator in eosinophilic diseases su
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
Costello, Jeff P.,Ferreira, Eric M.
supporting information, p. 9934 - 9939 (2019/12/24)
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
The versatile role of norbornene in C-H functionalization processes: concise synthesis of tetracyclic fused pyrroles via a threefold domino reaction
Gericke, Kersten M.,Chai, David I.,Lautens, Mark
, p. 6002 - 6014 (2008/12/20)
The synthesis of novel tetracyclic fused pyrroles from 1-(2-iodophenyl)-1H-pyrrole and various bromoalkyl-aryl alkynes via a palladium(0)-catalyzed and norbornene-mediated threefold domino reaction is reported. PdCl2 and tri-2-furylphosphine (TFP) in the presence of norbornene and Cs2CO3 in CH3CN at 90 °C gave a variety of tetracyclic fused pyrroles in usually high yields. In the described reaction sequence two of the three carbon-carbon bonds are formed by functionalization of an unactivated aryl C-H bond.
A facile synthesis of aryldihydropyrans using a Sonogashira-selenoetherification strategy
Brimble, Margaret A,Pavia, Gabrielle S,Stevenson, Ralph J
, p. 1735 - 1738 (2007/10/03)
A high yielding and convenient synthesis of 2-aryl-2,5-dihydro-2H-pyrans is reported. Sonogashira coupling of 4-pentyn-1-ol and 5-hexyn-2-ol with a range of phenyl and naphthyl bromides affords the appropriate aryl acetylenic alcohols which then undergo r
