89858-76-4Relevant academic research and scientific papers
Direct bromination and iodination of the trispyrazolyl borate ligand in TpRu(nbd)Cl and the effect of Tp4?X ligands on redox potentials and catalysis
Hattori, Hiroyuki,May, Jeremy A.
, (2020)
Traditional syntheses of Tp (trispyrazolylborate, HB(pz)3) ligands often require extreme conditions that are incompatible with some pyrazole derivatives. In contrast, an alternative direct functionalization of the Tp ligand could offer more compatible conditions. To prove this principle, direct bromination or iodination of TpRu(nbd)Cl is reported herein, and Sonogashira cross-coupling of the iodinated ligand with an alkyne could be performed at ambient temperature. This direct halogenation strategy allows rapid access to several halogenated Tp4?XRu(nbd)Cl derivatives from TpRu(nbd)Cl in a single step and to diversified ruthenium complexes having functionalized Tp ligands in minimal additional steps. The influence of the halogen substituents on the physical and chemical properties of the complexes was also examined. Ligand exchange in the presence of modified ligands was facile. Halogenation caused the standard reduction or oxidation potential to shift 200 mV in the positive direction and reduced efficacy in ruthenium catalyzed epoxyalkyne rearrangement during examination of a literature hypothesis relating catalysis to reduction and oxidation potentials.
SUBSTITUTED CYCLOALKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY
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Page/Page column 236; 237, (2020/11/12)
Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.
SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY
-
Page/Page column 328, (2020/11/12)
Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.
Palladium-catalyzed C-H homocoupling of furans and thiophenes using oxygen as the oxidant
Li, Na-Na,Zhang, Yan-Lei,Mao, Shuai,Gao, Ya-Ru,Guo, Dong-Dong,Wang, Yong-Qiang
supporting information, p. 2732 - 2735 (2014/06/09)
A general and efficient palladium-catalyzed intermolecular direct C-H homocoupling of furans and thiophenes has been developed. The reaction is characterized by using molecular oxygen as the sole oxidant and complete C5-position regioselectivity. Both C2- and C3-substituted furans or thiophenes are appropriate substrates. The approach provides a straightforward, facile, and economical route to bifurans and bithiophenes under mild reaction conditions.
"Flex-activated" mechanophores: Using polymer mechanochemistry to direct bond bending activation
Larsen, Michael B.,Boydston, Andrew J.
supporting information, p. 8189 - 8192 (2013/07/05)
We describe studies in mechanochemical transduction that probe the activation of bonds orthogonal to an elongated polymer main chain. Compression of mechanophore-cross-linked materials resulted in the release of small molecules via cleavage of covalent bonds that were not integral components of the elongated polymer segments. The reactivity is proposed to arise from the distribution of force through the cross-linking units of the polymer network and subsequent bond bending motions that are consistent with the geometric changes in the overall reaction. This departure from contemporary polymer mechanochemistry, in which activation is achieved primarily by force-induced bond elongation, is a first step toward mechanophores capable of releasing side-chain functionalities without inherently compromising the overall macromolecular architecture.
Wittig rearrangement of 3-furylmethyl ethers: Facile synthesis of 3-metyl-2-furylmethanols and 3-furylethanols
Tsubuki, Masayoshi,Okita, Hiroyuki,Kaneko, Kazunori,Shigihara, Atsushi,Honda, Toshio
experimental part, p. 433 - 444 (2009/09/30)
Wittig rearrangement of 3-furylmethyl ethers 1a-i was investigated. Deprotonation of 3-furylmethyl ethers 1a-i with bases, such as BuLi and LDA, occurred preferentially at the allylic, propargylic, benzylic positions and α-position adjacent to carbonyl gr
Efficient synthesis of functionalized furans via ruthenium-catalyzed cyclization of epoxyalkyne derivatives
Lo, Ching-Yu,Guo, Hongyun,Lian, Jian-Jou,Shen, Fwu-Ming,Liu, Rai-Shung
, p. 3930 - 3932 (2007/10/03)
Ruthenium catalyst TpRuPPh3(CH3CN)2Cl is found to effect the cyclization of epoxyalkynes to furans in the presence of Et3N. The reactions worked well for various epoxyalkynes with suitable oxygen and nitrogen functionalities with low loading of catalyst. It failed with disubstituted epoxyalkynes. The mechanism was elucidated by a deuterium labeling experiment that suggested that the mechanism involved a ruthenium-vinylidenium intermediate.
The diels-alder cycloaddition reaction of some substituted furans and E- 1,2-bis(phenylsulfonyl)ethylene
Arjona, Odon,Iradier, Fatima,Manas, Rosario M.,Plumet, Joaquin,Grabuleda, Xavier,Jaime, Carlos
, p. 9095 - 9110 (2007/10/03)
The Diels-Alder cycloaddition between several 2-, and 3-substituted furans and E-1,2-bis(phenylsulfonyl)ethylene have been carried out in high yields. Stereoselectivity observed in the case of 2-sustituted furans has been explained by means of the MM3-tra
Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes
Balasubramaniam, Rajiv P.,Moss, David K.,Wyatt, Justin K.,Spence, John D.,Gee, Arvin,Nantz, Michael H.
, p. 7429 - 7444 (2007/10/03)
Two chiral quaternary carbon-containing fragments suitable for elaboration to the briaran diterpenes were obtained by regioselective methylation of functionalized 3,3-disubstituted 2,3-epoxy-1-ols. The factors which favor methylation at the more hindered position of a trisubstituted 2,3-epoxy alcohol were determined.
Wittig rearrangement of J-furylmethyl ethers and its application to the synthesis of dendrolasin
Tsubuki,Okita,Honda
, p. 2135 - 2136 (2007/10/02)
The Wittig rearrangement of 3-furylmethyl ethers proceeds efficiently to give 3-methyl-2-furyl methanols or 3-furylethanols depending on the basicity of the butyllithium used; synthesis of dendrolasin is achieved with the 1,2-rearrangement of 3-furylmethy
