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Journal of Organic Chemistry

Giorgio La Sorella, Laura Sperni, Patrizia Canton, Lisa Coletti, Fabrizio Fabris, Giorgio Strukul, Alessandro Scarso
We report a facile, inexpensive and green method for the preparation of Pd nanoparticles in aqueous medium stabilized by anionic sulfonated surfactants sodium 1-dodecanesulfonate 1a, sodium dodecylbenzenesulfonate 1b, dioctyl sulfosuccinate sodium salt 1c and poly(ethylene glycol) 4-nonylphenyl-3-sulfopropyl ether potassium salt 1d simply obtained by stirring aqueous solutions of Pd(OAc)2 with the commercial anionic surfactants further treated under hydrogen atmosphere for variable times. The aqueous Pd nanoparticles solutions were tested in the selective hydrogenation reactions of aryl-alcohols, -aldehydes and -ketones leading to complete conversion to the deoxygenated products even in the absence of strong Brønsted acids in the reduction of aromatic aldehydes and ketones, in the controlled semi-hydrogenation of alkynes leading to alkenes and in the efficient hydro-dechlorination of aromatic substrates...
May 18, 2018: Journal of Organic Chemistry
Junior Gonzales, Naga Venkata Satya Dinesh Kumar Bhupathiraju, Daniel Hart, Man Yuen, Maria Pia Sifuentes, Bleron Samarxhiu, Mark Maranan, Naxhije Berisha, James Batteas, Charles Michael Drain
Chlorins have unique photophysical properties that are exploited in diverse biological and materials applications. De novo chlorin synthesis with specific exocyclic motifs can be challenging and many are not stable to photobleaching and/or oxidation. A facile approach to a stable synthetic chlorin with a fused N-methyl pyrrolidine uses cyclo addition of a sarcosine-based azomethine ylide on 5,10,15,20-tetrakis-(2,3,4,5,6-pentafluorophenyl)-porphyrin (TPPF20) is reported, but this approach has limitations. We report the synthesis of stable chlorin scaffolds starting with TPPF20 using a new glycine-based N-(hydroxymethyl)-N-methelenemethanideaminium ylide...
May 18, 2018: Journal of Organic Chemistry
Miaomiao Tian, Guangfan Zheng, Xuesen Fan, Xingwei Li
Redox-neutral synthesis of isoquinolinium salts via C-H activation of pre-synthesized or in situ formed imines and coupling with α-diazo ketoesters have been realized, where a zinc salt promotes cyclization as well as provides a counter anion. Under three-component conditions, both ketone and aldehydes are viable arene sources. The coupling of imines with diazo malonates under similar conditions afforded isoquinolin-3-ones as the coupling product.
May 18, 2018: Journal of Organic Chemistry
Shohei Yoshioka, Hiroshi Aoyama, Hiromichi Fujioka, Mitsuhiro Arisawa
We developed novel one-pot multiple Diels-Alder reactions, which are frequently used in the construction of six-membered rings in functional molecular synthesis. We report triple and double Diels-Alder reactions with styrene derivatives, where the secondary Diels-Alder reaction takes place at a different position from that of the conventional Wagner-Jauregg reaction.
May 18, 2018: Journal of Organic Chemistry
Qiu Sun, Yuan-Yuan Zhang, Jing Sun, Ying Han, Xiaodong Jia, Chao-Guo Yan
A highly efficient Cu-catalyzed 1,2-difunctionalization of various N-heteroarenes were developed with ether and alkyl hal-ide at ambient temperature. This transformation involves the combination of oxidative coupling by Cu/TBHP and reduc-tion process by DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). This method provides an efficient way to prepare various substituted dihydroazaarenes derivatives via a free-radical process.
May 18, 2018: Journal of Organic Chemistry
Wei Guo, Wen Tan, Mingming Zhao, Lvyin Zheng, Kailiang Tao, Deliang Chen, XiaoLin Fan
Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green "CN" sources is demonstrated. This transformation features nontoxic and inexpensive "CN" sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions...
May 18, 2018: Journal of Organic Chemistry
J Gracia-Vitoria, I Osante, C Cativiela, P Merino, T Tejero
No abstract text is available yet for this article.
May 18, 2018: Journal of Organic Chemistry
Andrea Savoldelli, Qianli Meng, Roberto Paolesse, Frank R Fronczek, Kevin Malcolm Smith, M Graça Henriques Vicente
A novel route for the synthesis of unsymmetrical benzo-fused BODIPYs is reported using 4,5,6,7-tetrafluoroisoindole as a precursor. The reactivity of the asymmetric 3,5-dibromo benzo-fused BODIPY was investigated under nucleophilic substitution and Pd(0)-catalyzed cross-coupling reaction conditions. In addition to the 3,5-bromines, one α-fluoro group on the benzo-fused ring can also be functionalized, and an unusual homocoupling with formation of a bisBODIPY was observed. This new class of fluorinated BODIPYs could find various applications in medicine and materials...
May 18, 2018: Journal of Organic Chemistry
Aleksandra Gerus, Katarzyna Ślepokura, Jarosław Panek, Aleksandra Turek, Jerzy Lisowski
The reactions of hexaazamacrocycle 1 with 2,6-bis(bromomethyl)pyridine or 2,6-bis[(tosyloxy)methyl)]pyridine in the presence of appropriate carbonates result in the formation of derivatives of cryptand 6 - enantiopure azacryptates of sodium and potassium. Crystal structures of these compounds indicate interaction of a metal ion with four pyridine nitrogen atoms and four tertiary amine atoms. The competition reactions monitored by NMR spectroscopy indicate preferential binding of Na+ over K+ as well as higher affinity of 6 for Na+ in comparison with the [2...
May 18, 2018: Journal of Organic Chemistry
Martina Menger, Dieter Lentz, Mathias Christmann
A concise and scalable five-step synthesis of vitepyrroloids A and B, two cytotoxic labdane diterpenoid alkaloids from Vitex trifolia, is presented. The presented approach features a Ni-catalyzed cross-electrophile coupling between a (+)-sclareolide-derived alkyl iodide and 3-bromo-2-cyanopyrrole.
May 18, 2018: Journal of Organic Chemistry
Ravindra Kumar Gupta, Ammathnadu Sudhakar Achalkumar
A high yielding microwave-assisted synthetic method to obtain unsymmetrical perylene diester monoimide (PEI), by treating the perylene tetrester (PTE) with requisite amine is reported. Perylene-based molecules are widely used in the construction of self-assembled supramolecular structures because of their propensity to aggregate under various conditions. In comparison to perylene bisimides (PBIs), PEIs are less studied in organic electronics/self-assembly due to the synthetic difficulty and low yields in their preparation...
May 18, 2018: Journal of Organic Chemistry
Jason Melidonie, Junzhi Liu, Yubin Fu, Jan J Weigand, Reinhard Berger, Xinliang Feng
One antiaromatic polycyclic hydrocarbon (PH) with and without solubilizing tert-butyl substituents, namely s-indaceno[2,1- a:6,5- a']dipyrene (IDPs), has been synthesized by a four-step protocol. The IDPs represent the longitudinal, peri-extension of the indeno[1,2- b]fluorene skeleton towards a planar 40 π-electron system. Their structures were unambiguously confirmed by X-ray crystallographic analysis. The optoelectronic properties were studied by UV/Vis absorption spectroscopy and cyclic voltammetry. These studies revealed that peri-fusion renders the IDP derivatives with a narrow optical energy gap of 1...
May 18, 2018: Journal of Organic Chemistry
Christian R Zwick, Hans Renata
Due to their unique molecular architecture, the manzacidins have been the subject of intense synthetic efforts in the past two decades. Here, we describe two synthetic approaches towards manzacidin C that center on the enzymatic hydroxylation of unprotected L-leucine. This study also resulted in the discovery of novel synthetic methodologies, including a photocatalytic C-H azidation of unprotected amino acids. Additionally, we describe the use of hydroxylated L-leucine in the preparation of various densely-substituted pyrrolidines...
May 17, 2018: Journal of Organic Chemistry
Ya-Xun Xin, Shen Pan, Yangen Huang, Xiu-Hua Xu, Feng-Ling Qing
The efficient copper-catalyzed sulfenylation and selenylation of 2,3-allenoic acids with disulfides or diselenides were developed, respectively. These reactions proceeded through tandem radical addition/intramolecular cyclization processes, affording a series of 4-sulfenylated and 4-selenylated butenolides in moderate to excellent yields. Moreover, 4-sulfonylated butenolides could be also obtained by sulfenylation of 2,3-allenoic acids and subsequent oxidation. Further transformation of the sulfur- and selenium-containing butenolides afforded the corresponding furan derivatives in good yields...
May 17, 2018: Journal of Organic Chemistry
Noah A Setterholm, Frank E McDonald
We describe regio- and stereoselective cycloisomerizations of alcohols tethered to epoxyalkenes, to construct alkene-substituted pyrans. These transformations are best catalyzed by Pd(PPh3)4 in the presence of phosphite ligands, and with diphenylphosphinic acid as an essential Brønsted acid co-catalyst for activation of the epoxyalkene.
May 17, 2018: Journal of Organic Chemistry
Lin-Su Wei, Guo-Xue He, Xiang-Fei Kong, Cheng-Xue Pan, Dong-Liang Mo, Gui-Fa Su
A series of 1,2- and 2,3-fused quinazolinones have been synthesized in good to excellent yields through gold-catalyzed selective hydroarylations of alkynyl quinazolinone-tethered pyrroles. The studies revealed that 1,2-fused quinazolinones were obtained through a 1,3-rearrangement and sequential 6-exo-trig cyclization of N1-alkynyl quinazolinone-tethered pyrroles while N3-alkynyl quinazolinone-tethered pyrroles went through 6-exo-dig or 7-endo-dig cyclizations directly to afford 2,3-fused quinazolinones. The fused quinazolinones could be prepared at gram scale in three steps from commercial ortho-aminobenzamide...
May 17, 2018: Journal of Organic Chemistry
Kun Liu, Hua-Jie Jiang, Na Li, Hui Li, Jing Wang, Zheng-Zhu Zhang, Jie Yu
The chiral Co(III)-complex-templated Brønsted acids were found to be efficient bifunctional phase-transfer catalysts for the highly enantioselective bromocyclization of protected tryptamines with readily available N-bromosuccinimide (NBS) under an air atmosphere. The 3-bromohexahydropyrrolo[2,3-b]indoles, which are key building blocks of cyclotryptamine alkaloids, were thus obtained in up to 95% yield and 93.5:6.5 er.
May 17, 2018: Journal of Organic Chemistry
Xiong Ding, Pengfei Wang
We have demonstrated that the 3-diethylaminobenzyl (DEABn) photolabile protecting group (PPG) is an effective and structurally simple PPG for releasing molecules in aqueous environment. In general, the photoreaction is clean, and the released substrate and the PPG product, i.e., 3-diethylaminobenzyl alcohol, are obtained in high yield. The clean photoreaction can also be achieved under mild ambient conditions with sunlight while the reactant is stable under indoor lighting. Release of two substrates from one PPG chromophore in aqueous solution has been demonstrated to be feasible...
May 17, 2018: Journal of Organic Chemistry
Abraham J Waldman, Emily P Balskus
The molecular architectures and potent bioactivities of diazo-containing natural products have attracted the interest of synthetic and biological chemists. Despite this attention, the biosynthetic enzymes involved in diazo group construction have not been identified. Here, we show the ATP-dependent enzyme CreM installs the diazo group in cremeomycin via late-stage N-N bond formation using nitrite. This finding should inspire efforts to use diazo-forming enzymes in biocatalysis and synthetic biology and enable genome-based discovery of new diazo-containing metabolites...
May 17, 2018: Journal of Organic Chemistry
Dan-Dan Li, Jia-Wei Zhang, Chun Cai
Palladium nanoparticles were firstly anchored on modified biopolymer as an efficient catalyst for biofuel upgradation. Fluorinated compounds was grafted onto cellulose to obtain amphiphilic supports for on water reactions. Pd catalyst was prepared by straightforward deposition of metal nanoparticles on modified cellulose. The catalyst exhibited excellent catalytic activity and selectivity in hydrodeoxygenation of vanillin (a typical model compound of lignin) to 2-methoxy-4-methylphenol under atmospheric hydrogen pressure in neat water without any other additives under mild conditions...
May 17, 2018: Journal of Organic Chemistry
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