35008-87-8Relevant academic research and scientific papers
Engaging Alkenes and Alkynes in Deaminative Alkyl-Alkyl and Alkyl-Vinyl Cross-Couplings of Alkylpyridinium Salts
Baker, Kristen M.,Lucas Baca, Diana,Plunkett, Shane,Daneker, Mitchell E.,Watson, Mary P.
, p. 9738 - 9741 (2019)
An alkyl-alkyl cross-coupling of Katritzky alkylpyridinium salts and organoboranes, formed in situ via hydroboration of alkenes, has been developed. This method utilizes the abundance of both alkyl amine precursors and alkenes to form C(sp3)-C(sp3) bonds. This strategy is also effective with alkynes, enabling a C(sp3)-C(sp2) cross-coupling. Under these mild conditions, a broad range of functional groups, including protic groups, is tolerated. As seen with previous alkylpyridinium cross-couplings, mechanistic studies support an alkyl radical intermediate.
Visible-Light Controlled Divergent Catalysis Using a Bench-Stable Cobalt(I) Hydride Complex
Beltran, Frédéric,Bergamaschi, Enrico,Teskey, Christopher J.
supporting information, p. 5180 - 5184 (2020/04/22)
While the use of visible light in conjunction with transition metal catalysis offers powerful opportunities to switch between on/-off states of catalytic activity, the next frontier would be the ability to switch the actual function of the catalyst and resulting products. Here we report such an example of multi-dimensional catalysis. Featuring an easily prepared, bench-stable cobalt(I) hydride complex in conjunction with pinacolborane, we can switch the reaction outcome between two widely employed transformations, olefin migration and hydroboration, with visible light as the trigger.
Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride
Murai, Masahito,Nishimura, Kengo,Takai, Kazuhiko
supporting information, p. 2769 - 2772 (2019/03/23)
The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylsty
IMIDAMIDE SPHINGOSINE KINASE INHIBITORS
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Page/Page column 26, (2012/09/05)
Imidamide (amidine) analogs that can inhibit the activity of sphingosine kinase 1 and sphingosine kinase 2 (SphK1 and SphK2) are provided. The compounds can prevent angiogenesis in tumors.
Development of amidine-based sphingosine kinase 1 nanomolar inhibitors and reduction of sphingosine 1-phosphate in human leukemia cells
Kennedy, Andrew J.,Mathews, Thomas P.,Kharel, Yugesh,Field, Saundra D.,Moyer, Morgan L.,East, James E.,Houck, Joseph D.,Lynch, Kevin R.,MacDonald, Timothy L.
experimental part, p. 3524 - 3548 (2011/07/07)
Sphingosine 1-phosphate (S1P) is a bioactive lipid that has been identified as an accelerant of cancer progression. The sphingosine kinases (SphKs) are the sole producers of S1P, and thus, SphK inhibitors may prove effective in cancer mitigation and chemosensitization. Of the two SphKs, SphK1 overexpression has been observed in a myriad of cancer cell lines and tissues and has been recognized as the presumptive target over that of the poorly characterized SphK2. Herein, we present the design and synthesis of amidine-based nanomolar SphK1 subtype-selective inhibitors. A homology model of SphK1, trained with this library of amidine inhibitors, was then used to predict the activity of additional, more potent, inhibitors. Lastly, select amidine inhibitors were validated in human leukemia U937 cells, where they significantly reduced endogenous S1P levels at nanomolar concentrations.
Synthesis of Cp*CH2PPh2 and its use as a ligand for the nickel-catalysed cross-coupling reaction of alkyl halides with aryl Grignard reagents
Uemura, Minoru,Yorimitsu, Hideki,Oshima, Koichiro
, p. 4726 - 4728 (2007/10/03)
A new ligand, Cp*CH2PPh2 (Cp* = 1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl), was prepared, and was used as a ligand for nickel-catalysed cross-coupling reaction of alkyl halides with aryl Grignard reagents, which nickel-phosphine complexes had never made possible. The Royal Society of Chemistry.
Palladium-catalyzed cyclization of ω-haloallenes. A new general route to common, medium, and large ring compounds via cyclic carbopalladation
Ma, Shengming,Negishi, Ei-Ichi
, p. 6345 - 6354 (2007/10/02)
A series of ω-haloallenes (4-32) as well as related ω-haloalkenes (41-45) were prepared through the application of known procedures. Their cyclization in the presence of a catalytic amount of Cl2Pd(PPh3)2, a base, e.g., K2CO3, and other appropriate reagents was investigated mostly under two sets of conditions (conditions I and II). The results summarized in Table 1 reveal the following: (1) The Pd-catalyzed cyclization reaction of ω-haloallenes gives the desired five- through twelve-membered and twenty-membered ring products in respectable yields. (2) The use of the dilute solution technique and n-Bu4NCl is advantageous in the synthesis of eight-membered and larger rings. (3) Formation of a carbon-carbon bond uniformly takes place at the central carbon of an allene. (4) The corresponding reaction of ω-haloalkenes fails to give eight- and nine-membered rings and displays an intriguing endo - exo cyclization mode vs ring size profile. (5) The eight-membered ring products were exclusively Z, and the eleven-, twelve-, and twenty-membered ring products were E. The stereochemistry of the nine- and ten-membered rings depends on other factors as well. The putative allylpalladium intermediates can be trapped with external nucleophiles, such as malonate esters, organostannanes, phenols, and amines, to give the corresponding derivatives. The results support the oxidative addition - carbopalladation mechanism leading to the formation of allylpalladium intermediates. The results also indicate that the extents of the actual cyclization process itself may be considerably higher than indicated by the yields of the dehydropalladation products and that some undesirable side reactions, such as double bond isomerization, can be circumvented through trapping with nucleophiles.
