1087-49-6Relevant articles and documents
Glassy carbon modified by a silver-palladium alloy: cheap and convenient cathodes for the selective reductive homocoupling of alkyl iodides
Poizot, Philippe,Jouikov, Viatcheslav,Simonet, Jacques
, p. 822 - 824 (2009)
Micrometer-thick layers of silver-palladium alloy were elaborated in order to modify the surface of glassy carbon electrodes. Such a surface modification can be readily achieved via a preliminary silver galvanostatic deposit onto carbon followed by a 'palladization' step, thanks to a simple immersion in acidic PdII-based solutions producing a displacement reaction. The as-prepared metallic interfaces exhibit outstanding catalytic capabilities especially in the cleavage of carbon-halogen bonds while being chemically/electrochemically quite stable and relatively inexpensive. More specifically, the use of such glassy carbon/Ag-Pd electrodes in dimethylformamide (DMF) containing tetraalkylammonium salts (TAA+X-) makes the one-electron reductions of primary alkyl iodides possible; this reduction leads to the formation of homodimers in high yields. Formation of a free radical as transient resulted from the homocoupling reaction.
Zn-mediated decarboxylative carbagermatranation of aliphatic: N -hydroxyphthalimide esters: Evidence for an alkylzinc intermediate
Jiang, Wei-Tao,Yang, Shuo,Xu, Meng-Yu,Xie, Xiu-Ying,Xiao, Bin
, p. 488 - 493 (2020)
Alkyl nucleophiles synthesized by decarboxylation of the corresponding N-hydroxyphthalimide esters (NHP esters) would inherit the complex structure of natural carboxylic acids and result in useful cross-coupling fragments. Herein, we report the synthesis
Synthesis of Asymmetrical-Terminally Bifunctionlized Alkanes by Sequential Suzuki–Miyaura Coupling Using B-Thexylboracyclanes
Suzuki, Ryota,Fuse, Shinichiro,Tanaka, Hiroshi
, p. 3478 - 3481 (2016)
A one-pot, sequential Suzuki–Miyaura coupling (SMC) using B-thexylboracyclanes is reported. We focused on a boracyclane with a bulky B-substituent as an equivalent of a terminal heterobibora-functionalized spacer. The first SMC of the boracyclane proceeded by endocyclic B–C bond cleavage due to the steric hindrance of the exocyclic B-substituent to provide borinic acids. These subsequently underwent the second SMC under harsher conditions by transfer of the less hindered primary alkyl group to provide the asymmetrically bifunctionalized alkyl chain. The seven- to five-membered boracyclanes were adaptable to the sequential SMC reactions to provide terminally bifunctional alkanes, although the efficiency of the transformation of the five-membered boracyclane was poorer than those of the others. To demonstrate the utility of the method, we successfully prepared several terminally heterobifunctional hexanes in a one-pot reaction.
Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling
Barth, Emily L.,Charboneau, David J.,Germe, Cameron C.,Hazari, Nilay,Huang, Haotian,Mercado, Brandon Q.,Uehling, Mycah R.,Zultanski, Susan L.
, p. 21024 - 21036 (2021/12/14)
The syntheses of four new tunable homogeneous organic reductants based on a tetraaminoethylene scaffold are reported. The new reductants have enhanced air stability compared to current homogeneous reductants for metal-mediated reductive transformations, such as cross-electrophile coupling (XEC), and are solids at room temperature. In particular, the weakest reductant is indefinitely stable in air and has a reduction potential of -0.85 V versus ferrocene, which is significantly milder than conventional reductants used in XEC. All of the new reductants can facilitate C(sp2)-C(sp3) Ni-catalyzed XEC reactions and are compatible with complex substrates that are relevant to medicinal chemistry. The reductants span a range of nearly 0.5 V in reduction potential, which allows for control over the rate of electron transfer events in XEC. Specifically, we report a new strategy for controlled alkyl radical generation in Ni-catalyzed C(sp2)-C(sp3) XEC. The key to our approach is to tune the rate of alkyl radical generation from Katritzky salts, which liberate alkyl radicals upon single electron reduction, by varying the redox potentials of the reductant and Katritzky salt utilized in catalysis. Using our method, we perform XEC reactions between benzylic Katritzky salts and aryl halides. The method tolerates a variety of functional groups, some of which are particularly challenging for most XEC transformations. Overall, we expect that our new reductants will both replace conventional homogeneous reductants in current reductive transformations due to their stability and relatively facile synthesis and lead to the development of novel synthetic methods due to their tunability.
Iron-Based Catalyst for Borylation of Unactivated Alkyl Halides without Using Highly Basic Organometallic Reagents
Siddiqui, Sheema,Bhawar, Ramesh,Geetharani
, p. 1948 - 1954 (2021/01/14)
The mild borylation of alkyl bromides and chlorides with bis(neopentylglycolato)diborane (B2neop2) mediated by iron-bis amide is described. The reaction proceeds with a broad substrate scope and good functional group compatibility. Moreover, sufficient ca
