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.
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
Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis
Chen, Cheng,Lu, Hongjian,Shi, Zhuangzhi,Wang, Minyan,Zhao, Binlin
, p. 21756 - 21760 (2021/08/30)
Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)?C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper-catalyzed Kumada reactions.
