- Sensing of alkylating agents using organic field-effect transistors
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Alkylating agents are simple and reactive molecules that are commonly used in many and diverse fields, such as organic synthesis, medicine and agriculture. Some highly reactive alkylating species are also being used as blister chemical warfare agents. The detection and identification of alkylating agent is not a trivial issue because of their high reactivity and simple structure. Here, a novel polythiophene derivative that is capable of reacting with alkylating agents is reported, along with its application in direct electrical sensing of alkylators using an organic field-effect transistor, OFET, device. Upon reacting with alkylators, the OFET containing the new polythiophene analogue as its channel becomes conductive, and the gate effect is lost; this is in marked contrast to the response of the OFET to innocent vapors, such as alcohols and acetone. By following the drain-source current under gate bias, one can easily follow the processes of absorption of the analyte to the polythiophene channel and their subsequent reaction.
- Gannot, Yair,Hertzog-Ronen, Carmit,Tessler, Nir,Eichen, Yoav
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Read Online
- Palladium-Catalyzed Electrophilic Functionalization of Pyridine Derivatives through Phosphonium Salts
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Herein, we report a highly efficient and practical method for pyridine-derived heterobiaryl synthesis through palladium-catalyzed electrophilic functionalization of easily available pyridine-derived quaternary phosphonium salts. The nice generality of this reaction was goes beyond arylation, enabling facile incorporation of diverse carbon-based fragments, including alkenyl, alkynyl, and also allyl fragments, onto the pyridine core. Notably, the silver salt additive is revealed to be of vital importance for the success of this transformation and its pivotal role as transmetallation mediator, which guarantees a smooth transfer of pyridyl group to palladium intermediate, is also described.
- Che, Yuan-Yuan,Deng, Xuezu,Feng, Chao,Lin, Ling-Zhi,Pei, Bingbing,Yue, Yanni
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supporting information
p. 16414 - 16419
(2020/07/20)
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- Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
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A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
- Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
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supporting information
(2019/05/07)
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- Water based surfactant-assisted synthesis of thienylpyridines and thienylbipyridine intermediates
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The connection between heterocyclic systems by forming new C[sbnd]C bond is a relevant topic for the easy preparation of intermediates and functional dyes for technological applications. Several methods were developed in the last decades and the urge for sustainable synthetic chemical methods pushed us to prepare thienylpyridines and two thienylbipyridine ligands by the Suzuki reaction in aqueous CTAB micellar medium and in presence of a Pd catalyst. These intermediates can be found as component of dyes and functional thiophene monomers. Reaction conditions were optimized under both thermal and microwave (MW) activation obtaining good yields (70–93%) using Pd(PPh3)4 as catalyst. Two thienylbipyridine ligands were prepared and the transformation of one of them into a terthiophene-based bipyridine ligand was easily obtained by almost green methods and with very good yield. This clean and sustainable method can be proposed as a green step to obtain intermediates and final dyes for technological applications, such as CO2 reduction, in gram-multigram scale.
- Quagliotto,Barbero,Barolo,Buscaino,Carfora,Prosperini,Viscardi
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p. 468 - 479
(2016/12/16)
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- An N-Heterocyclic Carbene-Nickel Half-Sandwich Complex as a Precatalyst for Suzuki-Miyaura Coupling of Aryl/Heteroaryl Halides with Aryl/Heteroarylboronic Acids
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A nickel half-sandwich complex supported by our original NHC ligand was developed as a robust precatalyst for Suzuki-Miyaura cross-coupling. The addition of PPh3 was a crucial element in the suppression of side reactions and in accelerating the cross-coupling reaction. By employing the optimal conditions, aryl-aryl, heteroaryl-aryl, and heteroaryl-heteroaryl couplings were achieved.
- Ando, Shin,Matsunaga, Hirofumi,Ishizuka, Tadao
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p. 1266 - 1272
(2018/06/18)
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- Phosphonium Salts as Pseudohalides: Regioselective Nickel-Catalyzed Cross-Coupling of Complex Pyridines and Diazines
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Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross-couplings compared to halides, enabling chemoselective palladium- and nickel-catalyzed coupling sequences.
- Zhang, Xuan,McNally, Andrew
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p. 9833 - 9836
(2017/08/08)
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- Reactive polythiophenes with zincke salt structure: Synthesis, polymer reactions, and chemical properties
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Polythiophenes with reactive Zincke salt structure, such as PThThPy +DNP(Cl-)Th, were synthesized by the oxidation polymerization of 3'-(4-N-(2,4-dinitrophenyl)pyridinium chloride)-2,2':5', 2″-terthiophene (ThThPy+DNP(Cl-)Th) with iron(III) chloride or copper(II) trifluoromethanesulfonate. The reaction of PThThPy +DNP(Cl-)Th with R-NH2 (R = n-hexyl (Hex) and phenyl (Ph)) substituted the 2,4-dinitrophenyl group into the R group with the elimination of 2,4-dinitroaniline to yield PThThPy+R(Cl -)Th. Similarly, model compounds, ThThPy+R(Cl -)Th (R = Hex and Ph), were also synthesized. In contrast to the photoluminescent ThThPyTh and PThThPyTh, the compounds PThThPy +DNP(Cl-)Th, PThThPy+R(Cl-)Th, and ThThPy+R(Cl-)Th showed no photoluminescence because their internal pyridinium rings acted as quenchers. Cyclic voltammetry measurements suggested that PThThPy+DNP(Cl-)Th received an electrochemical reduction of the pyridinium and 2,4-dinitrophenyl groups and oxidation of the polymer backbone. PThThPy+DNP(Cl-)Th was electrically conductive (ρ = 2.0 × 10-6 S cm-1) in the non-doped state.
- Yamaguchi, Isao,Nakahara, Takuya
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scheme or table
p. 3340 - 3349
(2012/08/29)
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- DABO boronates: Stable heterocyclic boronic acid complexes for use in suzuki-miyaura cross-coupling reactions
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Diethanolamine-complexed heterocyclic boronic acids (DABO boronates) are air-stable reagents that can be used directly in Suzuki-Miyaura reactions in the presence of water or a protic co-solvent. Interestingly, heterocyclic DABO boronates can be stored for extended periods of time at room temperature with no noticeable degradation, unlike their boronic acid counterparts. Heterocyclic DABO boronates constitute an operationally simple and efficient alternative to other boronic acid derivatives as coupling partners in palladium-catalyzed cross-coupling reactions under standard Suzuki-Miyaura conditions. Georg Thieme Verlag Stuttgart - New York.
- Reilly, Maureen K.,Rychnovsky, Scott D.
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p. 2392 - 2396
(2011/11/05)
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- Detection and identification of alkylating agents by using a bioinspired "chemical nose"
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Alkylating agents are simple and reactive molecules that are commonly used in many and diverse fields such as organic synthesis, medicine, and agriculture. Some highly reactive alkylating species are also being used as blister chemical-warfare agents. The
- Hertzog-Ronen, Carmit,Borzin, Elena,Gerchikov, Yulia,Tessler, Nir,Eichen, Yoav
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supporting information; experimental part
p. 10380 - 10386
(2010/04/25)
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- Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
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A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated.
- Billingsley, Kelvin,Buchwald, Stephen L.
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p. 3358 - 3366
(2007/10/03)
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- A CONVENIENT SYNTHESIS OF FIVE-MEMBERED HETEROARYL -SUBSTITUTED PYRIDINES
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Five-membered heteroarylpyridines (3) or (4) such as furylpyridines, thienylpyridines, imidazolylpyridines and pyrrolylpyridines were obtained regioselectively in appreciable yields (40-67percent) by reaction of heteroaryllithium salts with N-ethoxycarbonylpyridinium chloride (1) followed by oxygen oxidation.
- Shiao, Min- Jen,Shih, Li- Hua,Chia, Win- Long,Chau, Tay- Yuan
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p. 2111 - 2118
(2007/10/02)
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- PHOTOREACTION OF 4-IODOPYRIDINE WITH HETEROAROMATICS
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Photoreaction of 4-iodopyridine with various heteroaromatics leads to give corresponding 4-heteroarylpyridines in appreciable yields.
- Seki, Koh-ichi,Ohkura, Kazue,Terashima, Masanao
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p. 799 - 803
(2007/10/02)
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