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Issue 8, From the journal: Chemical Communications. You have access to this article. Please wait while we load your content Something went wrong. Try again? Cited by. Download options Please wait Supplementary information PDF K. Article type Communication. Submitted 04 Dec Accepted 04 Jan First published 04 Jan Download Citation. Request permissions. A highly efficient waterborne photoinitiator for visible-light-induced three-dimensional printing of hydrogels J.

Social activity. Search articles by author Jieping Wang. Sascha Stanic. Altan Alpay Altun.

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The estimated time of arrival ETA is a critical task in the intelligent transportation system, which involves the spatiotemporal data. Despite a significant amount of prior efforts have been made to design efficient and accurate systems for ETA task, few of them take structural graph data into account, much less the heterogeneous information network. Specifically, we translate the road map into a multi-relational network and introduce a vehicle-trajectories based network to jointly consider the traffic behavior pattern.

Moreover, we employ three components to model temporal information from recent periods, daily periods and weekly periods respectively. Each component comprises temporal convolutions and graph convolutions to learn representations of the spatiotemporal heterogeneous information for ETA task.

Experiments on large-scale datasets illustrate the effectiveness of the proposed HetETA beyond the state-of-the-art methods, and show the importance of representation learning of heterogeneous information networks for ETA task.

A general approach to site-specific, intramolecular C-H functionalization using dithiocarbamates. Morcillo, S. Photoinduced remote functionalization of amides and amines using electrophilic nitrogen radicals. Groendyke, B.

Li, Z. Copper-catalyzed arylation of remote C sp 3 -H bonds in carboxamides and sulfonamides. Zhang, Z. Katohgi, M. New synthetic method to 1,2-benzisothiazolineone-1,1-dioxides and 1,2-benzisothiazolineoneoxides from N-Alkyl o-methyl arenesulfonamides.

Tetrahedron 55 , � Fan, R. Yang, M. Silver-catalysed direct amination of unactivated C�H bonds of functionalized molecules. Paz, N. Chemoselective intramolecular functionalization of methyl groups in nonconstrained molecules promoted by N-iodosulfonamides. Richers, J. Qin, Q. Visible-light-promoted remote C sp 3 -H amidation and chlorination. Wappes, E. Reddy, L. Liu, T. Copper-catalyzed bromination of C sp 3 -H bonds distal to functional groups. Short, M. Shu, W. Yuan, W. Asymmetric alkylation of remote C sp 3 -H bonds by combining proton-coupled electron transfer with chiral Lewis acid catalysis.

Friese, F. Zhou, T. Silver-catalyzed long-distance aryl migration from carbon center to nitrogen center. Guin, J. Thiol-catalyzed stereoselective transfer hydroamination of olefins with N-aminated dihydropyridines. Chou, C. Radical-transfer hydroamination of olefins with N-aminated dihydropyridines.

Asian J. Piou, T. Palladium-catalyzed through-space C sp 3 -H and C sp 2 H bond activation by 1,4-palladium migration: efficient synthesis of [3,4]-fused oxindoles. Wu, K. Azidation in the difunctionalization of olefins.

Molecules 21 , Studer, A. Merino, E. Addition of CF 3 across unsaturated moieties: a powerful functionalization tool.

Charpentier, J. Electrophilic trifluoromethylation by use of hypervalent iodine reagents. Huang, X. Bunescu, A. Copper-catalyzed three-component carboazidation of alkenes with acetonitrile and sodium azide. Bao, X. Copper-catalyzed methylative difunctionalization of alkenes. Kochi, J.

Catalytic reactions of peroxides: direct initiation by Cuprous Species. Tetrahedron 24 , � Verma, A. Transition metal free intramolecular selective oxidative C sp 3 -N coupling: synthesis of N-Aryl-isoindolinones from 2-alkylbenzamides. Nouawa-Kumada, K. Copper-catalyzed sp 3 C-H aminative cyclization of 2-alkyl-N-arylbenzamides: an approach for the synthesis of N-Aryl-isoindolinones.

Yu, P. Feng, C. Direct directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes. Download references. You can also search for this author in PubMed Google Scholar. Correspondence to Jieping Zhu. Journal peer review information : Nature Communications thanks Sangit Kumar, Wei Yu and the other anonymous reviewer for their contribution to the peer review of this work. Reprints and Permissions. Copper-catalyzed remote C sp 3 �H azidation and oxidative trifluoromethylation of benzohydrazides.

Nat Commun 10 , Download citation. Received : 05 November Accepted : 15 January Published : 15 February Anyone you share the following link with will be able to read this content:. Sorry, a shareable link is not currently available for this article. Provided by the Springer Nature SharedIt content-sharing initiative. By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Sign up for the Nature Briefing newsletter � what matters in science, free to your inbox daily. Skip to main content Thank you for visiting nature. Download PDF. Similar articles being viewed by others. Functionalization of remote C sp3 -H bonds enabled by copper-catalyzed coupling of O-acyloximes with terminal alkynes 21 January Copper-catalyzed carbo-difluoromethylation of alkenes via radical relay 01 June Copper-catalysed benzylic C�H coupling with alcohols via radical relay enabled by redox buffering 24 February Site-selective remote C sp3 �H heteroarylation of amides via organic photoredox catalysis 18 October Site-specific allylic C�H bond functionalization with a copper-bound N-centred radical 23 October Direct arylation of strong aliphatic C�H bonds 01 August Subjects Catalytic mechanisms Homogeneous catalysis Synthetic chemistry methodology.

Full size image. Data availability The authors declare that the data supporting the findings of this study are available within the paper and the Supplementary Information, as well as from the authors upon request. References Hofman, A. Article Google Scholar Chu, J. Article Google Scholar Zhang, H. Article Google Scholar Studer, A. Article Google Scholar Bunescu, A. View author publications. Ethics declarations Competing interests The authors declare no competing interests.

Additional information Journal peer review information : Nature Communications thanks Sangit Kumar, Wei Yu and the other anonymous reviewer for their contribution to the peer review of this work.

Supplementary information. Supplementary Information. About this article. Cite this article Bao, X. Copy to clipboard.

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Among many available synthetic methodologies, the Sonogashira reaction is one of the most reliable transformations for the synthesis of internal alkynes 2. In a different approach, in situ oxidation of N , N -dimethylaniline derivatives to the corresponding iminiums followed by nucleophilic addition of copper acetylides has been developed for the synthesis of propargylamines Fig. The direct alkynylation of remote unfunctionalized sp 3 carbon by terminal alkynes remains, to the best of our knowledge, unknown.

Using nitrogen-centered radicals NCRs as precursors of carbon-centered radicals has become the focus of recent intense research efforts 11 , 12 , 13 , In this context, redox-active acyclic 15 and cyclic 16 oxime derivatives, pioneered by Forrester and Zard, respectively, have been demonstrated to be versatile precursors of iminyl radicals under either oxidative or reductive conditions.

The resulting carbon radicals can then be trapped by radical acceptors, affording remote C sp 3 functionalized alkylnitriles and ketones.

For example, terminal alkynes have been used as radical acceptors by Chen and Xiao for the synthesis of functionalized dihydronaphthalenes Fig. Stimulated by the challenges associated with the direct alkynylation of unfunctionalized remote sp 3 carbon, we became interested in alkynylation of oxime esters with terminal alkynes. The underline principle is outlined in Fig.

Reduction of O -acyloximes 1 cyclic or 2 acyclic by copper acetylide A , formed in situ from terminal alkyne 3 and Cu I species, would afford Cu II intermediate B and iminyl radical C. Facile reductive elimination from E would furnish the alkynylated product with concurrent regeneration of the Cu I catalytic species. In this catalytic cycle, copper went through three oxidation states and the high-valent Cu III species, difficult to access by classic oxidative addition, would be formed via a SET process.

Although most of radical�Cu II rebound processes involved activated secondary or tertiary benzylic carbons 42 , 43 , 44 , we have very recently shown that it is also possible to functionalize the primary radical in the presence of copper under photocatalysis conditions 45 , We began our studies by investigating the reductive alkynylation of cyclobutanone oxime esters with phenylacetylene 3a.

After systematic survey of the ester groups, the copper sources, the ligands, the bases, the temperature, and the solvents with or without Blue LEDs irradiation Supplementary Methods, Tables 1 � 7 , the optimum conditions found consisted of performing the reaction of 1a with 3a in acetonitrile c 0. As shown in Fig. Alkynes attached to an heteroarene such as pyridine, indole, and even thiophene were compatible to afford alkynylated nitriles 4k � 4m in satisfactory yields. Aliphatic alkynes participated in the reaction to deliver the products 4o � 4u in good yields.

A range of functional groups, such as ester, amide, carbamate, sulfonamide bearing an acidic proton, were well tolerated. Performing the reaction of 1a with 3q at 2. Yields refer to the isolated products. The alkynylation protocol was next applied to a diverse set of oxime esters Fig. This result was not unexpected considering the reversibility of 1,5-HAT of iminyl radicals to benzylic radicals After an exhaustive optimization of reaction conditions see Supplementary Methods, Tables 8 � 14 , we found that stirring a DCE solution of 2a 0.

The generality of this protocol is shown in Fig. Oxime esters derived from aliphatic ketones 5q � 5t were selectively alkynylated at the benzylic position. Functional groups such as terminal alkyne 5t , nitrile 5s , thioether 5ae , enyne 5ag , alkyl chloride 5ac , and heteroarenes 5u � 5w were well tolerated. Alkynylation on a tertiary carbon was also feasible 5af , albeit with reduced yield.

An experiment performed at 1. One solution to this problem is to perform the reaction under acidic conditions 15 , 33 , 39 , which are unfortunately incompatible with the present alkynylation conditions. Application of these protocols to the late-stage functionalization of natural product-derived alkynes was examined.

Control experiments were conducted to gain insights on the possible reaction mechanism. The results of these control experiments indicated clearly the existence of the radical intermediates and the feasibility of the reaction pathway depicted in Fig. To address this limitation, we proposed to combine this radical chemistry with the powerful transition metal-catalyzed cross-coupling reaction, and demonstrated that capture of the C radical by organocopper salts followed by reductive elimination of the resulting Cu III intermediate is a highly efficient way to functionalize the translocated C radical.

The catalytic amount of copper played a triple roles: it reacted with terminal alkyne to form the copper I acetylide, which in turn served as a reductant to reduce the oxime ester to generate the iminyl radical and the Cu II species.

Reductive elimination of the latter afforded the remote alkynylated alkylnitriles or ketones with the concurrent regeneration of the Cu I species. O -acyloximes 1 0. The reaction vessel was evacuated and filled up with nitrogen three times, then CH 3 CN 1. A suspension of O -acyloximes 2 0. Alkyne 3 0.

The combined organic layers were washed with aqueous NH 4 Cl solution, dried over Na 2 SO 4 , and evaporated to dryness under reduced pressure. The authors declare that the data supporting the findings of this study are available within the paper and the Supplementary Information, as well as from the authors upon request. Galm, U. Antitumor antibiotics: bleomycin, enediynes, and mitomycin.

Sonogashira, K. Cross-coupling reactions to sp carbon atoms. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines.

Tetrahedron Lett. Article Google Scholar. Okuro, K. Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes. Monnier, F. Copper-catalyzed Sonogashira-type reactions under mild palladium-free conditions. Eckhardt, M. The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides.

Vechorkin, O. Ni-Catalyzed Sonogashira coupling of nonactivated alkyl halides: orthogonal functionalization of alkyl iodides, bromides, and chlorides. Hazra, A. Photoinduced copper-catalyzed coupling of terminal alkynes and alkyl iodides. Liu, W. Empowering a transition-metal-free coupling between alkyne and alkyl iodide with light in water. Li, Z. CuBr-Catalyzed efficient alkynylation of sp 3 C-H bonds adjacent to a nitrogen atom.

Zard, S. Recent progress in the generation and use of nitrogen-centred radicals. Chen, J. Visible light photoredox-controlled reactions of N -radicals and radical ions. Davies, J. Hydroxylamine derivatives as nitrogen-radical precursors in visible-light photochemistry.

Stateman, L. Remote C-H functionalization via selective hydrogen atom transfer. Synthesis 50 , Forrester, A. Part 7. Perkin Trans. Boivin, J. Iminyl radicals: part II. Tetrahedron 50 , Nishimura, T. Iridium-catalyzed ring cleavage reaction of cyclobutanone O -benzoyloximes providing nitriles.

Li, L. Yang, H. Divergent iron-catalyzed coupling of O -acyloximes with silyl enol ethers. Gu, Y. Zhao, B. Copper-catalyzed intermolecular Heck-like coupling of cyclobutanone oximes initiated by selective C-C bond cleavage. Yu, X. Copper-catalyzed radical cross-coupling of redox-active oxime esters, styrenes, and boronic acids.

Wu, J. Copper-catalyzed redox-neutral cyanoalkylarylation of activated alkenes with cyclobutanone oxime esters.

Zhao, J. Photoinduced fragmentation-rearrangement sequence of cycloketoxime esters. Front 5 , Shen, X. Le Vaillant, F. Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers. Ding, D. Synthesis of gem-difluoroalkenes by merging Ni-catalyzed C-F and C-C bond activation in cross-electrophile coupling. He, Y. Dauncey, E. A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring opening-arylation, -vinylation and -alkylation cascades.

Photoinduced, copper-catalyzed radical cross-coupling of cycloketone oxime esters, alkenes, and terminal alkynes. Shu, W.

Visible-light-mediated remote aliphatic C-H functionalizations through a 1,5-hydrogen transfer cascade. A tag already exists with the provided branch name. Many Git commands accept both tag and branch names, so creating this branch may cause unexpected behavior.

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