- Self-Assembly of Chiral-at-End Diketopyrrolopyrroles: Symmetry Dependent Solution and Film Optical Activity and Photovoltaic Performance
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Chiral thiophene-diketopyrrolopyrrole derivatives have been synthesised to investigate the potential of stereochemistry and symmetry as a means of modulating properties by influencing self-assembly of these purely organic materials. In particular, derivatives of diketopyrrolopyrrole were employed because of their proven interest as dyes, especially for organic solar cells. The natural product myrtenal was used as the source of stereochemistry, introduced through a Kr?hnke reaction of a thiophene-bearing pyridinium salt and diketopyrrolopyrroles were prepared through Suzuki coupling with this chiral moiety at one end only as well as at both ends. Absorption spectroscopy and electrochemistry confirmed the potential suitability of the compounds for photovoltaic devices. The nanostructures formed by the compounds have been probed with circular dichroism spectroscopy in solution and in films. It is shown that a chiral C2 symmetric molecule assembles in solution giving a strong circular dichroic signal while as a film this optical activity is nulled, whereas an asymmetric homologue is most optically active as a thin film. The X-ray crystal structure of the asymmetric compound shows a polar order of the molecules that might explain this observation. The lack of optical activity in solution is very likely a result of the high solubility of the compound. The results reaffirm the sensitivity of circular dichroism spectroscopy to inter-chromophore organisation, whereas absorption spectroscopy in the visible region reveals only slight changes to the bands. The differing order in the compounds also affects their performance in bulk heterojunction photovoltaic devices. Atomic force microscopy of the blended thin films with the fullerene derivative usually employed (PC61BM) showed that smooth and well mixed films were achieved, with the conditions required during spin coating depending greatly on the derivative, because of their differing solubility. The apparently better performance of the symmetrical compound (although with very low efficiency) is probably a result of the alignment of the molecules inferred by the circular dichroism experiments, whereas the asymmetric compound presumably adopts a twisted supramolecular organisation.
- Hume, Paul A.,Monks, James P.,Pop, Flavia,Davies, E. Stephen,MacKenzie, Roderick C. I.,Amabilino, David B.
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- Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles
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Cyclization of tosylmethyl isocyanide with α-oxodithioesters in the presence of KOH is reported for the synthesis of 4-methylthio-5-acylthiazoles. Similarly, ethyl isocyanoacetate underwent cyclization with α-oxodithioesters to form 4-ethoxycarbonyl-5-acy
- Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.,Swaroop, Toreshettahally R.
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p. 1444 - 1450
(2020/04/27)
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- Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane
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The design of catalysts for asymmetric propargylations remains a challenging task, with only a handful of methods providing access to enantioenriched homopropargylic alcohols. In this work, guided by previously reported computational predictions, a set of
- Vaganov, Vladimir Yu.,Fukazawa, Yasuaki,Kondratyev, Nikolay S.,Shipilovskikh, Sergei A.,Wheeler, Steven E.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
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p. 5467 - 5474
(2020/10/19)
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- Stereoselective Synthesis of Atropisomeric Bipyridine N,N′-Dioxides by Oxidative Coupling
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Bipyridine N,N′-dioxide is a structural fragment found in many bioactive compounds. Furthermore, chiral analogues secured their place as powerful Lewis base catalysts. The scope of the existing methods for the synthesis of atropisomeric bipyridine N,N′-di
- Fukazawa, Yasuaki,Vaganov, Vladimir Yu.,Shipilovskikh, Sergei A.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
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supporting information
p. 4798 - 4802
(2019/06/17)
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- Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regio? selective Synthesis of 2-Methylthio-3-Aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles
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o-Phenylenediammines and o-Aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-Aryl/heteroarylquinoxalines and 2-Acylbenzoxazoles in 55-94percent and 45-86percent, respectively, in the presence of p-T
- Anil, Seegehally M,Kiran, Kuppalli R,Rangappa, Kanchugarakoppal S,Sadashiva, Maralinganadoddi P,Shruthi, Jeegundipattana B,Sukrutha, Kodipura P,Swaroop, Toreshettahally R
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p. 4205 - 4214
(2019/11/14)
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- Luminescent PtII Complexes of Tridentate Cyclometalating 2,5-Bis(aryl)-pyridine Ligands
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Bis-cyclometalated PtII complexes of dianionic 2,5-bis(aryl)-pyridine ligands (L1–6)2–, carrying various cyclometalating or pending aryl groups, are synthesised in two steps. The reactions of H2L protoligands with K2[PtCl4] in acetic acid give the mono-cyclometalated complexes [Pt(HL)Cl]2. Heating these complexes in hot DMSO (dimethyl sulfoxide) yields the double-cyclometalated DMSO complexes [Pt(L1–6)(DMSO)]. The reaction of [Pt(L4)(DMSO)] with N,N-dimethylimidazolium iodide in the presence of KOtBu as the base gives the carbene complex [Pt(L4)(Me2Imd)]. Detailed photophysical studies reveal the intense orange luminescence of these complexes in CH2Cl2 solution, with quantum yields up to 0.22, and increased quantum yields of up to 1.00 in glassy frozen CH2Cl2/MeOH (1:1) and up to 0.44 in PMMA matrices. Detailed electrochemistry (including spectroelectrochemistry) reveals reversible ligand-based first reductions at –2.1 to –2.3 V, irreversible Pt-centred oxidations at around 0.8 V and electrochemical band gaps of 2.8–3.0 eV. Further reduction waves at very negative potentials interfere with the solvent (THF with traces of water) discharge and can be traced, with UV/Vis spectroelectrochemistry, to Pt-centred reductions for the DMSO complexes and to a second ligand-centred reduction for the Me2Imd complex from. The photo/electrochemical properties can be roughly correlated with the ligand pattern and suggest their use in optoelectronic applications.
- Krause, Maren,Kourkoulos, Dimitrios,González-Abradelo, Darío,Meerholz, Klaus,Strassert, Cristian A.,Klein, Axel
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supporting information
p. 5215 - 5223
(2017/10/18)
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- Novel 2-aryl-4-(4′-hydroxyphenyl)-5H-indeno[1,2-b]pyridines as potent DNA non-intercalative topoisomerase catalytic inhibitors
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On the basis of previous reports on the importance of thienyl, furyl or phenol group substitution on 5H-indeno[1,2-b]pyridine skeleton, a new series of rigid 2-aryl-4-(4′-hydroxyphenyl)-5H-indeno[1,2-b]pyridine derivatives were systematically designed and
- Park, Seojeong,Kadayat, Tara Man,Jun, Kyu-Yeon,Thapa Magar, Til Bahadur,Bist, Ganesh,Shrestha, Aarajana,Lee, Eung-Seok,Kwon, Youngjoo
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- Synthesis and biological evaluation of 2-phenol-4-chlorophenyl-6-aryl pyridines as topoisomerase II inhibitors and cytotoxic agents
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A new series of 2-phenol-4-chlorophenyl-6-aryl pyridines were designed, synthesized, and evaluated for topoisomerase (topo) I and II inhibitory activities as well as cytotoxic activity against four different human cancer cell lines such as HCT15, T47D, DU
- Thapa, Pritam,Kadayat, Tara Man,Park, Seojeong,Shin, Somin,Thapa Magar, Til Bahadur,Bist, Ganesh,Shrestha, Aarajana,Na, Younghwa,Kwon, Youngjoo,Lee, Eung-Seok
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p. 145 - 159
(2016/05/24)
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- Synthesis of novel C3-linked β-carboline-pyridine derivatives employing khronke reaction: DNA-binding ability and molecular modeling studies
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A series of novel C3-linked β-carboline pyridine (BCP) derivatives have been synthesized via modified Khronke reaction and studied for their DNA-binding affinities. Among all the derivatives, compound 12f has shown significant enhancement in the DNA-binding affinity (ΔTm:6.3 oC and 6.5 oC at 0 h and 18 h incubation) in comparison to the standard Doxorubicin (ΔTm:2.4 oC and 2.6 oC at 0 h and 18 h incubation). This result suggested a strong intercalation with DNA double helix. Moreover, molecular modeling studies also showed that the planar β-carboline ring establishes π-π interactions with DNA base pairs and these interactions are further extended due to the presence of pyridine ring. The DNA intercalation has also been investigated for these compounds by molecular docking and the results are in agreement with thermal denaturation data.
- Shankaraiah, Nagula,Sharma, Pankaj,Pedapati, Srinivas,Nekkanti, Shalini,Srinivasulu, Vunnam,Kumar, Niggula Praveen,Kamal, Ahmed
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p. 335 - 342
(2016/04/04)
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- Monitoring the DNA by ruthenium complexes of heterocyclic N,S-donor ligands and evaluation of biological activities
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Neutral N,S-donor bidentate ligands have been synthesized and characterized by NMR and IR spectroscopic techniques. The ligands have been used to synthesized ruthenium(II) complexes ([Ru(L1–L6)PPh3)2Cl2/su
- Karia, Parag S.,Vekariya, Pankajkumar A.,Patidar, Anshul P.,Patel, Ravi R.,Patel, Mohan N.
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p. 1903 - 1914
(2016/10/21)
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- Design and synthesis of novel 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives, and their evaluation of topoisomerase inhibitory activity and cytotoxicity
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For the development of potential anticancer agents, we designed and synthesized 30 new 2,4-diaryl-5H-indeno[1,2-b]pyridine derivatives containing aryl moiety such as furyl, thienyl, pyridyl, and phenyl at 2- and 4-position of 5H-indeno[1,2-b]pyridine. The
- Kadayat, Tara Man,Park, Chanmi,Jun, Kyu-Yeon,Magar, Til Bahadur Thapa,Bist, Ganesh,Yoo, Han Young,Kwon, Youngjoo,Lee, Eung-Seok
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p. 160 - 173
(2015/02/19)
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- A series of novel terpyridine-skeleton molecule derivants inhibit tumor growth and metastasis by targeting topoisomerases
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A series of novel terpyridine-skeleton molecules containing conformational rigidity, 14 containing benzo[4,5]furo[3,2-b]pyridine core and 15 comprising chromeno[4,3-b]pyridine core, were synthesized, and their biological activities were evaluated. 3-(4-Ph
- Kwon, Han-Byeol,Park, Chanmi,Jeon, Kyung-Hwa,Lee, Eunyoung,Park, So-Eun,Jun, Kyu-Yeon,Kadayat, Tara Man,Thapa, Pritam,Karki, Radha,Na, Younghwa,Park, Mi Sun,Rho, Seung Bae,Lee, Eung-Seok,Kwon, Youngjoo
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p. 1100 - 1122
(2015/03/04)
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- Design and synthesis of conformationally constrained hydroxylated 4-phenyl-2-aryl chromenopyridines as novel and selective topoisomerase II-targeted antiproliferative agents
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To develop novel selective topoisomerase II inhibitors, we designed and synthesized a series of conformationally constrained hydroxylated 4-phenyl-2-aryl chromenopyridines and evaluated their topoisomerase inhibitory activity and cytotoxicity against thre
- Thapa, Pritam,Jun, Kyu-Yeon,Kadayat, Tara Man,Park, Chanmi,Zheng, Zhi,Thapa Magar, Til Bahadur,Bist, Ganesh,Shrestha, Aarajana,Na, Younghwa,Kwon, Youngjoo,Lee, Eung-Seok
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p. 6454 - 6466
(2015/10/05)
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- Modified 2,4-diaryl-5H-indeno[1,2-b]pyridines with hydroxyl and chlorine moiety: Synthesis, anticancer activity, and structure-activity relationship study
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As a part of ongoing studies in developing novel anticancer agents, a series of modified 2,4-diaryl-5H-indeno[1,2-b]pyridines were designed, and synthesized by introducing hydroxyl and chlorine moieties. They were evaluated for topoisomerase inhibitory ac
- Kadayat, Tara Man,Song, Chanju,Kwon, Youngjoo,Lee, Eung-Seok
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- Discovery of dihydroxylated 2,4-diphenyl-6-thiophen-2-yl-pyridine as a non-intercalative DNA-binding topoisomerase II-specific catalytic inhibitor
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We describe our rationale for designing specific catalytic inhibitors of topoisomerase II (topo II) over topoisomerase I (topo I). Based on 3D-QSAR studies of previously published dihydroxylated 2,4-diphenyl-6-aryl pyridine derivatives, 9 novel dihydroxyl
- Jun, Kyu-Yeon,Kwon, Hanbyeol,Park, So-Eun,Lee, Eunyoung,Karki, Radha,Thapa, Pritam,Lee, Jun-Ho,Lee, Eung-Seok,Kwon, Youngjoo
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p. 428 - 438
(2014/05/20)
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- DNA interaction and cytotoxic activities of square planar platinum(II) complexes with N, S-donor ligands
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The platinum(II) complexes with N, S-donor ligands have been synthesized and characterized by physicochemical methods viz. elemental, electronic, FT-IR, 1H NMR and LC-MS spectra. The binding mode and potency of the complexes with HS DNA (Herrin
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.,Thakor, Khyati P.
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supporting information
p. 261 - 267
(2014/04/03)
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- 2,4-Diaryl benzofuro[3,2-b]pyridine derivatives: Design, synthesis, and evaluation of topoisomerase inhibitory activity and cytotoxicity
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Designed and synthesized twenty-four 2,4-diaryl benzofuro[3,2-b]pyridine derivatives were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Various aryl groups such as phenyl, 2-
- Thapa, Pritam,Jahng, Yurngdong,Park, Pil-Hoon,Jee, Jun-Goo,Kwon, Youngjoo,Lee, Eung-Seok
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p. 3073 - 3082
(2014/01/06)
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- Design, synthesis, and antitumor evaluation of 2,4,6-triaryl pyridines containing chlorophenyl and phenolic moiety
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We have designed and synthesized a series of 2,4,6-triaryl pyridine derivatives containing chlorophenyl and phenolic moeity at 2- and 4- position of the central pyridine, respectively, resulting in a total of 42 compounds. They were evaluated for topoisom
- Thapa, Pritam,Karki, Radha,Yun, Minho,Kadayat, Tara Man,Lee, Eunyoung,Kwon, Han Byeol,Na, Younghwa,Cho, Won-Jea,Kim, Nam Doo,Jeong, Byeong-Seon,Kwon, Youngjoo,Lee, Eung-Seok
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experimental part
p. 123 - 136
(2012/07/27)
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- Cytotoxic, DNA interaction, SOD mimic, and antimicrobial activities of square pyramidal copper(II) complexes
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The copper(II) complexes with NS donor ligand and ciprofloxacin were synthesized. The synthesized complexes were characterized by physicochemical parameters like elemental and thermal analysis, electronic, FT-IR, and LC-MS spectroscopy. The complexes were
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.
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scheme or table
p. 1224 - 1232
(2012/08/13)
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- Interaction of drug based copper(II) complexes with Herring Sperm DNA and their biological activities
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Square pyramidal Cu(II) complexes with NS donor ligand and ciprofloxacin have been synthesized and characterized using analytical and spectral techniques. The synthesized complexes have been tested for their antimicrobial activity using double dilution te
- Patel, Mohan N.,Patel, Chintan R.,Joshi, Hardik N.
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p. 66 - 73,8
(2012/12/11)
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- Synthesis and characterization of a fluorescent polymer containing 2,6-bis(2-thienyl)pyridine moieties as a highly efficient sensor for Pd 2+ detection
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A novel conjugated polymer chemosensor 1 containing 2,6-bis(2-thienyl) pyridine has been synthesized and exhibits a high sensitivity and selectivity for palladium ion detection based on the fluorescent quenching effect.
- Liu, Bin,Bao, Yinyin,Du, Fanfan,Wang, Hu,Tian, Jiao,Bai, Ruke
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supporting information; experimental part
p. 1731 - 1733
(2011/03/22)
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- Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase i and II inhibitory activity, cytotoxicity, and structure-activity relationship
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Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well a
- Thapa, Uttam,Thapa, Pritam,Karki, Radha,Yun, Minho,Choi, Jae Hun,Jahng, Yurngdong,Lee, Eunyoung,Jeon, Kyung-Hwa,Na, Younghwa,Ha, Eun-Mi,Cho, Won-Jea,Kwon, Youngjoo,Lee, Eung-Seok
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experimental part
p. 3201 - 3209
(2011/07/31)
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- 2,6-Dithienyl-4-furyl pyridines: Synthesis, topoisomerase I and II inhibition, cytotoxicity, structure-activity relationship, and docking study
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For the development of novel antitumor agents, 2,6-dithienyl-4-furyl pyridine derivatives were prepared and evaluated for their topoisomerase I and II inhibitory activity as well as cytotoxicity against several human cancer cell lines. Among the 21 prepared compounds, compound 24 exhibited strong topoisomerase I inhibitory activity. In addition, a docking study with topoisomerase I and compound 24 was performed.
- Basnet, Arjun,Thapa, Pritam,Karki, Radha,Choi, Hoyoung,Choi, Jae Hun,Yun, Minho,Jeong, Byeong-Seon,Jahng, Yurngdong,Na, Younghwa,Cho, Won-Jea,Kwon, Youngjoo,Lee, Chong-Soon,Lee, Eung-Seok
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body text
p. 42 - 47
(2010/03/24)
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- Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of hydroxylated 2,4-diphenyl-6-aryl pyridines
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A new series of 2,4-diphenyl-6-aryl pyridines containing hydroxyl group(s) at the ortho, meta, or para position of the phenyl ring were synthesized, and evaluated for topoisomerase I and II inhibitory activity and cytotoxicity against several human cancer cell lines for the development of novel anticancer agents. Structure-activity relationship study revealed that the substitution of hydroxyl group(s) increased topoisomerase I and II inhibitory activity in the order of meta > para > ortho position. Substitution of hydroxyl group on the para position showed better cytotoxicity.
- Karki, Radha,Thapa, Pritam,Kang, Mi Jeong,Jeong, Tae Cheon,Nam, Jung Min,Kim, Hye-Lin,Na, Younghwa,Cho, Won-Jea,Kwon, Youngjoo,Lee, Eung-Seok
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experimental part
p. 3066 - 3077
(2010/07/06)
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- Synthesis of 2,6-diaryl-substituted pyridines and their antitumor activities
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For the development of novel antitumor agents, we designed and synthesized 2,6-diaryl-substituted pyridine derivatives bearing three aryl groups, which are the bioisosteres of terpyridine, and evaluated their biological activities. Most of the 18 prepared compounds showed moderate cytotoxicity against several human cancer cell lines. From the structure-activity relationships we may conclude that the number of aryl groups employed would be critical for their biological activities.
- Son, Jong-Keun,Zhao, Long-Xuan,Basnet, Arjun,Thapa, Pritam,Karki, Radha,Na, Younghwa,Jahng, Yurngdong,Jeong, Tae Cheon,Jeong, Byeong-Seon,Lee, Chong-Soon,Lee, Eung-Seok
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p. 675 - 682
(2008/09/20)
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- Chiral aryl pyridyl alcohols as enantioselective catalysts in the addition of diethylzinc to substituted benzaldehydes
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Chiral (5-aryl-10,10-dimethyl-6-aza-tricyclo[7.1.1.02,7]undeca- 2(7),3,5-trien-8-yl)-diphenyl-methanols were prepared from highly enantiopure (1R)-(+)-α-pinene (> 97% ee), and applied in the enantioselective addition of diethylzinc to substitut
- Chang, Tien-Chu,Chen, Chinpiao
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scheme or table
p. 606 - 615
(2009/05/11)
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- Synthesis, topoisomerase I inhibition and structure-activity relationship study of 2,4,6-trisubstituted pyridine derivatives
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For the development of new anticancer agents, phenyl, 2-pyridyl, 2-furyl, 2-thienyl, 2-furylvinyl and 2-thienylvinyl substituted derivatives on 2,4,6-position in pyridine moiety were prepared and evaluated for their topoisomerase I inhibitory activity. Among the thirteen prepared compounds, four compounds exhibited strong topoisomerase I inhibitory activity. A structure-activity relationship study indicated that the 2-thienyl-4- furylpyridine skeleton was important for topoisomerase I inhibitory activity.
- Zhao, Long-Xuan,Moon, Yoon-Soo,Basnet, Arjun,Kim, Eun-Kyung,Jahng, Yurngdong,Park, Jae Gyu,Jeong, Tae Cheon,Cho, Won-Jea,Choi, Sang-Un,Lee, Chong Ock,Lee, Sun-Young,Lee, Chong-Soon,Lee, Eung-Seok
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p. 1333 - 1337
(2007/10/03)
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- Tricyclic quinoxalines as potent kinase inhibitors of PDGFR kinase, Flt3 and Kit
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Here we report on novel quinoxalines as highly potent and selective inhibitors of the type III receptor tyrosine kinases PDGFR, FLT3, and KIT. These compounds, tricyclic quinoxalines, were generated in order to improve bioavailability over the highly hydrophobic bicyclic quinoxalines. Four of the highly active compounds were characterized in detail and are shown to inhibit PDGFR kinase activity of the isolated receptor as well as in intact cells in the sub-micromolar concentration range. We show that the most active inhibitor (compound 13, AGL 2043) is ~15-20 times more potent than its isomer (compound 14, AGL 2044). We therefore compared the three dimensional structures of the two compounds by X-ray crystallography. These compounds are also highly effective in blocking the kinase activity of FLT3, KIT, and the oncogenic protein Tel-PDGFR in intact cells. These compounds are potent inhibitors of the proliferation of pig heart smooth muscle cells. They fully arrest the growth of these cells and the effect is fully reversible. The chemical, biochemical and cellular properties of these compounds as well as the solubility properties make them suitable for development as anti-restenosis and anti-cancer agents.
- Gazit, Aviv,Yee, Kevin,Uecker, Andrea,Boehmer, Frank-D.,Sjoeblom, Tobias,Oestman, Arne,Waltenberger, Johannes,Golomb, Gershon,Banai, Shmuel,Heinrich, Michael C.,Levitzki, Alexander
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p. 2007 - 2018
(2007/10/03)
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- Co-ordination Chemistry of 2-Phenyl-6-(2-thienyl)pyridine and 2,6-Bis(2-thienyl)pyridine; New Ambidentate Ligands
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The new ligands 2-phenyl-6-(2-thienyl)pyridine (H2pthpy) and 2,6-bis(2-thienyl)pyridine (H2bthpy) exhibit a variety of reactivities with d8 transition-metal complexes.Reaction of H2bthpy with platinum(II) gives complexes in which the ligand adopts Hbthpy-C,N and bthpy-CNC bonding modes, wheras gold(III) converts the ligand into the dimer 5,5'-bis(6-(2-thienyl)-2-pyridyl>-2,2'-bithiophene.Palladium(II) gives mixtures of cyclometallated complexes and dimerised ligand.In contrast, H2pthpy reacts with platinum(II) to give metallated complexes in which the site of metallation is the phenyl rather than the thienyl ring.The reaction of H2pthpy with gold(III) results in clean conversion into the dimer 5,5'-bis(6-phenyl-2-pyridyl)-2,2'-bithiophene and a chlorinated derivative 2-(5-chloro-2-thienyl)-6-phenylpyridine.Once again mixtures of metallated product and ligand reaction products are obtained with palladium(II).
- Constable, Edwin C.,Henney, Roland P. G.,Tocher, Derek A.
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p. 2467 - 2474
(2007/10/02)
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