143029-45-2Relevant academic research and scientific papers
Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity**
Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.
supporting information, p. 21418 - 21425 (2021/08/25)
Herein, we disclose that electrochemical stimulation induces new photocatalytic activity from a range of structurally diverse conventional photocatalysts. These studies uncover a new electron-primed photoredox catalyst capable of promoting the reductive cleavage of strong C(sp2)?N and C(sp2)?O bonds. We illustrate several examples of the synthetic utility of these deeply reducing but otherwise safe and mild catalytic conditions. Finally, we employ electrochemical current measurements to perform a reaction progress kinetic analysis. This technique reveals that the improved activity of this new system is a consequence of an enhanced catalyst stability profile.
Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate
Hashizume, Daisuke,Hosoya, Takamitsu,Nakamura, Kei,Ohmiya, Hirohisa,Sato, Yukiya,Sumida, Yuto
supporting information, p. 9938 - 9943 (2020/06/27)
The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.
Access to "friedel-Crafts-Restricted" tert -alkyl aromatics by activation/methylation of tertiary benzylic alcohols
Hartsel, Joshua A.,Craft, Derek T.,Chen, Qiao-Hong,Ma, Ming,Carlier, Paul R.
, p. 3127 - 3133 (2012/05/20)
Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)
Lohre, Claudia,Droege, Thomas,Wang, Congyang,Glorius, Frank
supporting information; experimental part, p. 6052 - 6055 (2011/06/25)
Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization
An eco-sustainable erbium(III) triflate catalyzed formation and cleavage of tert -butyl ethers
Procopio, Antonio,Costanzo, Paola,Curini, Massimo,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina
supporting information; experimental part, p. 73 - 78 (2011/03/19)
An eco-compatible method, which permits the formation or cleavage of tert-butyl ethers of alcohols and phenols, is proposed. The protection step is performed in solvent-free conditions at room temperature using catalytic amount of Er(OTf)3. The catalyst is easily- recovered from the aqueous phase and reused several times without significant loss of activity. The deprotection step developed is also highly eco-friendly since the tert-butyl group is removed very quickly from alcohols and phenols in methanol using MW irradiation-. Georg Thieme Verlag Stuttgart · New York.
3-(1',1'-Dimethylbutyl)-1-deoxy-Δ8-THC and related compounds: Synthesis of selective ligands for the CB2 receptor
Huffman, John W.,Liddle, John,Yu, Shu,Aung, Mie Mie,Abood, Mary E.,Wiley, Jenny L.,Martin, Billy R.
, p. 2905 - 2914 (2007/10/03)
The synthesis and pharmacology of 15 1-deoxy-Δ8-THC analogues, several of which have high affinity for the CB2 receptor, are described. The deoxy cannabinoids include 1-deoxy-11-hydroxy-Δ8-THC (5), 1-deoxy-Δ8-THC (6), 1-deoxy-3-butyl-Δ8-THC (7), 1-deoxy-3-hexyl-Δ8-THC (8) and a series of 3-(1',1'-dimethylalkyl)-1-deoxy-Δ8-THC analogues (2, n=0-4, 6, 7, where n=the number of carbon atoms in the side chain-2). Three derivatives (17-19Scheme 3(a) (C6H5)3PCH3+ Br-, n-BuLi/THF, 65°C; (b) LiAlH4/THF, 25°C; (c) KBH(sec-Bu)3/THF, -78 to 25°C then H2O2/NaOH.) of deoxynabilone (16) were also prepared. The affinities of each compound for the CB1 and CB2 receptors were determined employing previously described procedures. Five of the 3-(1',1'-dimethylalkyl)-1-deoxy-Δ8-THC analogues (2, n=1-5) have high affinity (K(i)=2 receptor. Four of them (2, n=1-4) also have little affinity for the CB1 receptor (K(i)=>295nM). 3-(1',1'-Dimethylbutyl)-1-deoxy-Δ8-THC (2, n=2) has very high affinity for the CB2 receptor (K(i)=3.4±1.0nM) and little affinity for the CB1 receptor (K(i)=677±132nM). Copyright (C) 1999 Elsevier Science Ltd.
Synthesis, structure and properties of various molecules based on the 4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzo[cd,mn]pyrene system with an evaluation of the effect differing molecular substitution patterns has on the space group symmetry
Faldt, Andre,Krebs, Frederik C.,Thorup, Niels
, p. 2219 - 2227 (2007/10/03)
4,8,12-Trioxa-4,8,12,12c-tetrahydrodibenzo[cd,mn]pyrene(3),2,6,10-tri-tert- butyl-4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzo[cd,mn]pyrene (11) and 2,6,10-tri-tert-butyl-4,8,12-trioxa-12c-methyl-4,8,12,12c-tetrahydrodibenzo[cd, mn]pyrene (12) have been syn
Neuroprotective (+) 3S, 4S cannabinoids with modified 5'-side chain
Pop, Emil,Browne, Clinton E.,Nadler, Varda,Biegon, Anat,Brewster, Marcus E.
, p. 1553 - 1558 (2007/10/03)
The synthesis and evaluation of two novel cannabinoids belonging to the (+) 3S, 4S nonpsychotropic series are described. These derivatives bind to the NMDA receptor but have lower affinities than dexanabinol (HU-211), the series benchmark. The novel compounds protect neurons against MDA- induced toxicity in cortical cell cultures and have lower toxicity to host neurons than dexanabinol.
