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Organic Letters

Cheoljae Kim, Brian A Ondrusek, Hoyong Chung
A highly removable N-heterocyclic carbene ligand for a transition-metal catalyst in aqueous media via host-guest interactions has been developed. Water-soluble adamantyl tethered ethylene glycol in the ligand leads a hydrophobic inclusion into the cavity of β-cyclodextrin. Ruthenium (Ru) olefin metathesis catalyst with this ligand demonstrated excellent performance in various metathesis reactions in water as well as in CH2Cl2, and removal of residual Ru was performed via filtration utilizing a host-guest interaction and extraction...
January 19, 2018: Organic Letters
Shuichi Nakamura, Daiki Hayama, Masataka Miura, Tsubasa Hatanaka, Yasuhiro Funahashi
The first catalytic enantioselective reaction of 2H-azirines with thiols has been developed. The obtained aziridines can be converted to optically active oxazolines, aziridylamides, or α-sulfonyl esters. Transformation of these optically active aziridines showed that 2H-azirines act as β,β-dicarbocationic amine synthons.
January 19, 2018: Organic Letters
Yingbo Shi, Yang Ji, Kunyun Xin, Shuanhu Gao
The first total synthesis of (-)-xestosaprol N and O is described. This synthetic work features a convergent strategy: (1) a Pd-catalyzed arylation followed by cyclization to build a naphthalene fragment (ring C, D); (2) utilization of (-)-quinic acid to construct the chiral hydroxyl group at C-2; (3) a substrate controlled intramolecular Heck reaction to construct a quaternary carbon center (ring B); (4) introduction of a hypotaurine moiety at a late stage to furnish the E ring.
January 19, 2018: Organic Letters
Andrei Nikolaev, Claude Y Legault, Minhao Zhang, Arturo Orellana
A well-defined homogeneous silver precatalyst can be utilized for the direct C-H functionalization of a wide range of aromatic nitrogen heterocycles with cyclopropanols under acid-free conditions. This reaction can be conducted on gram-scale and with low catalyst loadings (as low as 1%), which is rare for silver-catalyzed Minisci-type reactions. Moreover, reactivity trends, as well as steric and calculated electronic properties of the heterocycles, strongly suggest that silver-heterocycle complexes formed in situ behave as redox active catalysts and as Lewis acid activators of the heterocycle and that the electronic nature of the heterocyclic substrates tunes the reactivity of the resulting complexes...
January 19, 2018: Organic Letters
Milind M Ahire, Mahesh B Thoke, Santosh B Mhaske
A novel reactivity of sulfur ylides has been demonstrated in a transition-metal-free protocol to access ortho-substituted thioanisole derivatives by insertion of arynes into a C-S σ-bond in moderate to good yields. The reaction involves the formation of C-C and C-S bonds and consecutive breaking of two C-S bonds under operationally mild reaction conditions.
January 19, 2018: Organic Letters
Dino Berthold, Bernhard Breit
The rhodium-catalyzed asymmetric N1-selective and regioselective coupling of triazole derivatives with internal alkynes and terminal allenes gives access to secondary and tertiary allylic triazoles in very good enantioselectivities. For this process, three new members of the JosPOphos ligand family have been prepared and employed in catalysis. The optimized reaction conditions enable the coupling of triazoles with internal alkynes as well as with allenes, displaying a high tolerance for functional groups. A gram scale reaction provided N1-allyltriazole, which was subjected to various transformations highlighting synthetic utility...
January 19, 2018: Organic Letters
Katharina Zielke, Mario Waser
The first (4 + 1)-annulation of o-quinone methides with α-branched allenoates as C1 synthons has been developed. This operationally simple protocol gives access to highly functionalized dihydrobenzofurans in an unprecedented fashion with excellent diastereoselectivities and high yields.
January 19, 2018: Organic Letters
Tian-Jun Gong, Meng-Yu Xu, Shang-Hai Yu, Chu-Guo Yu, Wei Su, Xi Lu, Bin Xiao, Yao Fu
An example of Rh-catalyzed C-H activation with methyl trifluoroacrylate for the synthesis of fluoroolefins and heterocycles (benzoindolizines) is reported. The types of products were determined by the directing group. The benzoindolizines and fluoroolefins were obtained by using pyridine and pyrazole as the directing group, correspondingly. These transformations present a number of advantages, such as oxidant-free reaction conditions and broad functional group tolerance. Moreover, this reaction greatly extends the application of fluoroolefins...
January 19, 2018: Organic Letters
Georgia A Zissimou, Andreas Kourtellaris, Panayiotis A Koutentis
Isodiphenylfluorindine (5) reacts with K2Cr2O7/H+ to give 13-oxoisodiphenylfluorindinium perchlorate (7) (75%), but with phenyliodine bis(trifluoroacetate) (PIFA) or MnO2 it gives the zwitterionic and quinoidal cruciform 13,13'-dimers 11 (85%) and 12 (89%), respectively. The zwitterionic 13,13'-dimer 11 can be rapidly converted with MnO2 into the quinoidal 13,13'-dimer 12 (100%). UV-vis, NMR, single-crystal X-ray diffraction, and density functional theory studies support the structural assignments of all products...
January 19, 2018: Organic Letters
Guang-Zu Wang, Rui Shang, Yao Fu
It is reported that Pd(PPh3)2Cl2 in combination with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) under irradiation of blue LEDs efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl heteroarenes with aliphatic N-(acyloxy)phthalimides at room temperature. A broad scope of secondary, tertiary, and quaternary carboxylates, including α-amino acid derived esters, can be applied as amenable substrates with high stereoselectivity. The experimental observation was explained by excitation-state reactivity of the palladium complex under irradiation to induce single-electron transfer to activate N-(acyloxy)phthalimides, and to suppress undesired β-hydride elimination of alkyl palladium intermediates...
January 18, 2018: Organic Letters
Florian Mäsing, Harald Nüsse, Jürgen Klingauf, Armido Studer
Silyl ketones were used for the preparation of palladium nanoparticles (PdNPs) starting with Pd(OAc)2 in dimethylformamide under irradiation with a visible light-emitting diode (LED). Variation of the silyl ketone structure allowed adjustment of the PdNP diameter (1.9 or 5.2 nm). The in situ-formed PdNPs were further stabilized with polyvinylpyrrolidone and then applied as recyclable catalysts in the Suzuki-Miyaura coupling of arylboronic acids with aryl iodides to obtain substituted biphenyls in excellent yields...
January 18, 2018: Organic Letters
Dong Hyuk Kim, Juyoung Lee, Anna Lee
An efficient one-pot approach for the synthesis of diaryl sulfoxides and diaryl sulfones using aryl thiols and aryl diazonium salts was developed. The use of a visible-light-driven silver catalysis and the subsequent singlet-oxygen-induced oxidation enabled selective synthesis of sulfoxides and sulfones in the absence of a photocatalyst. The reactions were carried out under mild reaction conditions; the desired products were obtained under air atmosphere at room temperature.
January 18, 2018: Organic Letters
Penglin Wu, Minqiang Jia, Weilong Lin, Shengming Ma
The ring opening-coupling reaction of cyclopropanols with propargylic carbonates affording synthetically attractive allenyl ketones has been developed. The mechanism involves the ligand-exchange reaction of in situ formed allenyl palladium methoxide with cyclopropanols followed by carbon-carbon bond cleavage and reductive elimination. The reactions proceeded smoothly under mild reaction conditions with Pd(0)/XPhos catalysis in the absence of any external base and displayed a wide scope and application to a steroidal skeleton...
January 18, 2018: Organic Letters
Edward Richmond, Vuk D Vuković, Joseph Moran
A general, Brønsted acid catalyzed method for the room temperature, nucleophilic ring opening of donor-acceptor cyclopropanes in fluorinated alcohol solvent, HFIP, is described. Salient features of this method include an expanded cyclopropane scope, including those bearing single keto-acceptor groups and those bearing electron-deficient aryl groups. Notably, the catalytic system proved amenable to a wide range of nucleophiles including arenes, indoles, azides, diketones, and alcohols.
January 18, 2018: Organic Letters
Osama El-Sepelgy, Aleksandra Brzozowska, Jan Sklyaruk, Yoon Kyung Jang, Viktoriia Zubar, Magnus Rueping
A new iron-catalyzed chemoselective intramolecular hydroamination and hydroalkoxylation of the readily available α-allenic amines and alcohols to valuable unsaturated 5-membered heterocycles, 2,3-dihydropyrrole and 2,3-dihydrofuran, is reported. Effective selectivity control is achieved by a metal-ligand cooperative activation of the substrates. The mild reaction conditions and the use of low amounts of an air and moisture stable iron catalyst allow for the hydrofunctionalization of a wide range of allenes bearing different functional groups in good yields in the absence of base or any sensitive additives...
January 18, 2018: Organic Letters
Jia-Li Liu, Ze-Fan Zhu, Feng Liu
An efficient and mild oxycyanation of vinyl ethers with 2,2,6,6-tetramethyl-N-oxopiperidinium and TMSCN is described. The mechanistic studies indicated that the formation of an electron donor-acceptor complex and subsequent single-electron-transfer process could be involved in the reaction.
January 18, 2018: Organic Letters
Akhil Padarti, Dongeun Kim, Hyunsoo Han
A distinctly different approach for the vinylogous aldolation of aldehydes is described, which exploits 2-oxonia-Cope rearrangement reactions between two readily available partners, a set of rationally designed chiral homoallylic alcohol synthons and aldehydes, under simple conditions. In these processes, chirality transfer from the former to the latter is nearly perfect, giving rise to excellent enantio- and diastereoselectivity without the regioselectivity issue associated with traditional vinylogous aldol reactions...
January 18, 2018: Organic Letters
Promod Kumar, Anup Kumar Sharma, Tirumaleswararao Guntreddi, Rahul Singh, Krishna Nand Singh
A novel regiospecific C(sp3)-C(sp2) coupling between ethyl arylacetates and nitroarenes has been developed to deliver biaryl ketones in excellent yields. The protocol is metal-free, mild, and compatible with a number of functional groups on both of the reacting partners.
January 18, 2018: Organic Letters
Yohei Saito, Masuo Goto, Kyoko Nakagawa-Goto
The first total synthesis of parvifloron F, a bioactive highly oxidized abietane diterpene, was achieved. The abietane skeleton was constructed by Lewis acid promoted cyclization. Preliminary structure-activity relationship correlations were established for the synthetic intermediates against human tumor cell lines. Certain compounds showed unique selective antiproliferative activity against triple-negative breast cancer. The oxidation level of the abietane ring affected the selectivity.
January 18, 2018: Organic Letters
Min Wu, Juan Li, Ruqin Zhang, Xia Tian, Zhaoxiang Han, Xiaoqing Lu, Kunpeng Guo, Zhike Liu, Zhongqiang Wang
Two spiroannulated molecular structures with dithiafulvenyl units functionalized at the 2,2',7,7'- (SFX-DTF1) and 2,3',6,'7- (SFX-DTF2) positions of a spiro[fluorene-9,9'-xanthene] core were synthesized. Studies revealed the hole mobility was significantly influenced by the dithiafulvenyl functionalized positions in the molecular structure. To explore their primary applications as hole-transporting materials in perovskite solar cells, SFX-DTF1-based devices exhibited a power conversion efficiency of 10.67% without the use of p-type dopants, yielding good air stability...
January 18, 2018: Organic Letters
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