- Palladium-catalyzed allylation of tautomerizable heterocycles with alkynes
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A method for the allylic amidation of tautomerizable heterocycles was developed by a palladium catalyzed allylation reaction with 100% atom economy. A series of structurally diverse N-allylic substituted heterocycles can be synthesized in good yields with high chemo-, regio-, and stereoselectivities under mild conditions.
- Lu, Chuan-Jun,Chen, Dong-Kai,Chen, Hong,Wang, Hong,Jin, Hongwei,Huang, Xifu,Gao, Jianrong
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- Enantioselective Addition of α-Nitroesters to Alkynes
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By using Rh–H catalysis, we couple α-nitroesters and alkynes to prepare α-amino-acid precursors. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a RhIII–π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α-disubstituted α-amino esters.
- Davison, Ryan T.,Parker, Patrick D.,Hou, Xintong,Chung, Crystal P.,Augustine, Sara A.,Dong, Vy M.
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supporting information
p. 4599 - 4603
(2021/01/18)
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- Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides
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An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.
- Du, Wu-Bo,Wang, Ning-Ning,Pan, Chao,Ni, Shao-Fei,Wen, Li-Rong,Li, Ming,Zhang, Lin-Bao
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supporting information
p. 2420 - 2426
(2021/04/07)
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- Palladium-catalyzed methylation of terminal alkynes
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In this communication, a palladium-catalyzed procedure for the methylation of terminal alkynes has been developed. With N,N,N-trimethylbenzenaminium trifluoromethanesulfonate as the methyl source, various desired products were obtained in moderate to good yields. Both aromatic and aliphatic alkynes are applicable.
- Wang, Wei-Feng,Wu, Xiao-Feng
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- Rh-Catalyzed Asymmetric Hydrogenation of α,β- and β,β-Disubstituted Unsaturated Boronate Esters
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A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully transformed to the corresponding chiral alcohols, amines and other important derivatives with maintained enantioselectivities.
- Hou, Guohua,Shen, Xin,Yan, Qiaozhi,Zi, Guofu
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supporting information
(2020/05/08)
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- Direct Synthesis of 1-Arylprop-1-ynes with Calcium Carbide as an Acetylene Source
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A simple method is described for the synthesis of 1-arylprop-1-ynes directly from aromatic aldehyde p -tosylhydrazones by using calcium carbide as an acetylene source. The salient features of this protocol are its use of a readily available and easily handled source of acetylene, its operational simplicity, its high yield, and its broad substrate scope.
- Gao, Lei,Li, Zheng
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supporting information
p. 1580 - 1584
(2019/08/20)
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- Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive
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Convenient access to diverse libraries of internal alkynes via decarboxylative Sonogashira reaction of alkynyl-carboxylic acids with iodoarenes, employing imidazolium-ILs as solvent, along with piperidine-appended imidazolium [PAIM][NTf2] as task-specific basic IL is demonstrated, without the need for any ligand or additive. The feasibility to perform these reactions by sequential one-pot iododediazoniation/decarboxylative Sonogashira reaction is also shown, and the scope of the methods is underscored by providing 29 examples. The potential for recycling and reuse of the IL solvent is also examined.
- Prabhala, Pavankumar,Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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p. 2061 - 2064
(2019/03/07)
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- Blue Light Induced Difluoroalkylation of Alkynes and Alkenes
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The difluoroalkylation of alkynes and alkenes by direct photoexcitation of ethyl difluoroiodoacetate is described. Under catalyst- and oxidant-free conditions, iododifluoroalkylation and hydrodifluoroalkylation products were generated from alkynes, and difluoroalkylation products were prepared from alkenes. This methodology provides a streamlined access to difluoroalkylated organic compounds starting from simple alkynes or alkenes.
- Li, Kangkui,Zhang, Xuexin,Chen, Jingchao,Gao, Yang,Yang, Chunhui,Zhang, Keyang,Zhou, Yongyun,Fan, Baomin
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supporting information
p. 9914 - 9918
(2019/12/24)
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- A Pd-catalyzed domino Larock annulation/dearomative Heck reaction
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A palladium-catalyzed domino Larock annulation/dearomative Heck reaction is developed, which delivers a range of tetracyclic indoline derivatives in moderate to excellent yields through a Larock annulation of N-bromobenzoyl o-iodoanilines with alkynes and a subsequent intramolecular dearomative Heck reaction. This protocol provides a straightforward route to structurally diverse indolines from readily available starting materials by forming two new rings and three chemical bonds in a single step.
- Liang, Ren-Xiao,Xu, Deng-Yun,Yang, Fu-Ming,Jia, Yi-Xia
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supporting information
p. 7711 - 7714
(2019/07/09)
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- Indium-mediated Palladium-catalyzed Allylic Alkylation of Isatins with Alkynes
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An unprecedented indium-mediated palladium-catalyzed allylic alkylation of isatins with alkynes is disclosed. This reaction provides a new, practical, and straightforward route to access 3-allyl-3-hydroxy-2-oxindoles in good yields with broad substrate scope and scalability, exhibiting high atom and step economy. A primary mechanistic study reveals that indium played two roles in the reaction, first as a reductant and second as a Lewis acid. Compared with previous methods, our strategy eliminated the steps for the separation and purification of the reaction intermediates, as well as pre-installing leaving groups to allylic substrates. Moreover, our reaction did not employ moisture-sensitive allylic metal species and stoichiometric oxidants. (Figure presented.).
- Wu, Zijun,Fang, Xinxin,Leng, Yuning,Yao, Hequan,Lin, Aijun
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supporting information
p. 1289 - 1295
(2018/02/21)
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- Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex
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The molybdenum and tungsten complexes M2(OR)6 (Mo2F6, M = Mo, R = C(CF3)2Me; W2F3, M = W, R = OC(CF3)Me2) were synthesized as bimetallic congeners of the highly active alkyne metathesis catalysts [MesC-M{OC(CF3)nMe3-n}] (MoF6, M = Mo, n = 2; WF3, M = W, n = 1; Mes = 2,4,6-trimethylphenyl). The corresponding benzylidyne complex [PhC-W{OC(CF3)Me2}] (WPhF3) was prepared by cleaving the W-W bond in W2F3 with 1-phenyl-1-propyne. The catalytic alkyne metathesis activity of these metal complexes was determined in the self-metathesis, ring-closing alkyne metathesis and cross-metathesis of internal and terminal alkynes, revealing an almost equally high metathesis activity for the bimetallic tungsten complex W2F3 and the alkylidyne complex WPhF3. In contrast, Mo2F6 displayed no significant activity in alkyne metathesis.
- Ehrhorn, Henrike,Schl?sser, Janin,Bockfeld, Dirk,Tamm, Matthias
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p. 2425 - 2434
(2018/10/04)
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- Multi-Metal-Catalyzed Oxidative Radical Alkynylation with Terminal Alkynes: A New Strategy for C(sp3)-C(sp) Bond Formation
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A new way for C(sp3)-C(sp) cross-coupling with terminal alkynes has been developed by using a multi-metal-catalyzed reaction strategy. Alkyl radicals generated from different approaches are able to couple with terminal alkynes by judicious selection of the catalyst combination. This reaction protocol offers an efficient alternative approach for the synthesis of substituted alkynes from terminal alkynes besides traditional Sonogashira coupling. Mechanistic studies have also been carried out to clarify the role of each metal catalyst in the radical alkynylation processes. The reactions were found to go through radical reaction pathways. Synergistic cooperation of the metal catalysts is the key for controlling the reaction selectivity of alkyl radicals toward C(sp3)-C(sp) bond formation.
- Tang, Shan,Liu, Yichang,Gao, Xinlong,Wang, Pan,Huang, Pengfei,Lei, Aiwen
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supporting information
p. 6006 - 6013
(2018/05/14)
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- High Oxidation State Molybdenum N-Heterocyclic Carbene Alkylidyne Complexes: Synthesis, Mechanistic Studies, and Reactivity
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The first synthetic protocol to high oxidation state molybdenum(VI) N-heterocyclic carbene (NHC) alkylidyne complexes (NHC=1,3-diisopropylimidazol-2-ylidene, 1,3-dimethyl-4,5-R2-imidazol-2-ylidene, R2=H, Cl, CN) is reported. Steric limitations of the NHCs and the benzylidyne are described. All novel complexes were characterized by single crystal X-ray diffraction and solution NMR techniques. It was shown that all complexes presented here show activity in the self-metathesis of 1-phenyl-1-propyne at room temperature. To identify mechanistic differences, an experimental sequence to detect dissociation of ligands was developed. Results reveal dissociation of less electron-donating NHCs in course of the reaction. Mechanistic and reactivity differences were attributed to electronic and steric effects through Tolman's electronic parameter and the percentage of buried volume. Furthermore, Mo-1 containing the 1,3-dimethylimidazol-2-ylidene ligand showed good activity in self-metathesis reactions of p-substituted 1-phenyl-1-propynes with electron-donating moieties at room temperature.
- Koy, Maximilian,Elser, Iris,Meisner, Jan,Frey, Wolfgang,Wurst, Klaus,K?stner, Johannes,Buchmeiser, Michael R.
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supporting information
p. 15484 - 15490
(2017/11/09)
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- Rhodium-Catalyzed Intermolecular Carbonylative [2 + 2 + 1] Cycloaddition of Alkynes Using Alcohol as the Carbon Monoxide Source for the Formation of Cyclopentenones
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A highly regioselective rhodium-catalyzed intermolecular carbonylative [2 + 2 + 1] cycloaddition of alkynes using alcohol as a CO surrogate to access 4-methylene-2-cyclopenten-1-ones has been developed. In this transformation, the alcohol performs multiple roles, including generating the Rh-H intermediate, functioning as the CO source, and assisting in the isomerization of the alkyne. Alkynes can act as both the olefin and the alkyne partner in the cyclopentenone core.
- Kim, Ju Hyun,Song, Taemoon,Chung, Young Keun
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supporting information
p. 1248 - 1251
(2017/03/14)
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- Palladium-catalyzed allylic alkylation with internal alkynes to construct C-C and C-N bonds in water
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A palladium-catalyzed system enabled efficient allylic alkylation with alkynes in water has been developed. This reaction presents an environmentally friendly strategy for constructing lots of allylic compounds with indolinones, ketones, amines as well as electron-rich aromatic compounds as nucleophiles. Moreover, the in situ formed arylallene intermediate adopting alkynes as starting materials omits the need for leaving groups and extra oxidants, showing high atom economy. The versatility of the developed reaction also lends itself to the incorporation of deuteriums by simply replacing H2O with D2O.
- Gao, Shang,Liu, Hao,Wu, Zijun,Yao, Hequan,Lin, Aijun
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supporting information
p. 1861 - 1865
(2017/06/09)
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- Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates
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Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.
- Yoneyama, Hiroki,Numata, Masahiro,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
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p. 5538 - 5556
(2017/06/07)
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- Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes to Synthesize Indolenines with C3-Quarternary Centers
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A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C-H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.
- Gao, Shang,Wu, Zijun,Fang, Xinxin,Lin, Aijun,Yao, Hequan
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supporting information
p. 3906 - 3909
(2016/08/16)
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- Engineering P450 Peroxygenase to Catalyze Highly Enantioselective Epoxidation of cis-β-Methylstyrenes
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P450 119 peroxygenase and its site-directed mutants are discovered to catalyze the enantioselective epoxidation of methyl-substituted styrenes. Two new site-directed P450 119 mutants, namely T213Y and T213M, which were designed to improve the enantioselectivity and activity for the epoxidation of styrene and its methyl substituted derivatives, were studied. The T213M mutant is found to be the first engineered P450 peroxygenase that shows highly enantioselective epoxidation of cis-β-methylstyrenes, with up to 91 % ee. Molecular modeling studies provide insights into the different catalytic activity of the T213M mutant and the T213Y mutant in the epoxidation of cis-β-methylstyrene. The results of the calculations also contribute to a better understanding of the substrate specificity and configuration control for the regio- and stereoselective peroxygenation catalyzed by the T213M mutant.
- Zhang, Chun,Liu, Ping-Xian,Huang, Lu-Yi,Wei, Si-Ping,Wang, Li,Yang, Sheng-Yong,Yu, Xiao-Qi,Pu, Lin,Wang, Qin
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supporting information
p. 10969 - 10975
(2016/07/27)
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- Organomagnesium-catalyzed isomerization of terminal alkynes to allenes and internal alkynes
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Organomagnesium complexes 2 were synthesized from N,N-dialkylamineimine ligands 1 and dibenzylmagnesium by benzylation of the imine moiety. 3-Aryl-1-propynes reacted with 2 to form the corresponding tetraalkynyl complexes, which acted as catalysts for the transformation of these terminal alkynes into allenes and further to internal alkynes under mild conditions. To the best of our knowledge, this example is the first of an organomagnesium-catalyzed isomerization of alkynes. Notably, the reactions proceeded through temporally separated autotandem catalysis, thus allowing the isolation of the allene or internal alkyne species in good yields. Mechanistic experiments suggested that the catalytically active tetraalkynyl complexes consist of a tautomeric mixture of alkynyl-, allenyl-, and propargylmagnesium species.
- Rochat, Rapha?l,Yamamoto, Koji,Lopez, Michael J.,Nagae, Haruki,Tsurugi, Hayato,Mashima, Kazushi
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supporting information
p. 8112 - 8120
(2015/05/27)
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- Palladium-catalyzed methylation of alkynyl C(sp)-H bonds with dimethyl sulfonium ylides
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A novel palladium-catalyzed methylation protocol for the synthesis of methyl-functionalized internal alkynes has been established. This methylation method is achieved through a C(sp)-C(sp3) bond formation process and represents a new synthetic application of sulfonium ylides.
- Liu, Yan-Yun,Yang, Xu-Heng,Huang, Xiao-Cheng,Wei, Wen-Ting,Song, Ren-Jie,Li, Jin-Heng
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p. 10421 - 10426
(2013/11/06)
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- Ni-catalyzed alkenylation of triazolopyridines: Synthesis of 2,6-disubstituted pyridines
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A synthetic strategy to access 2,6-disubstituted pyridines from triazolopyridines through a regioselective nickel-catalyzed alkenylation reaction of the C7-H bond is described. The N2 fragment embedded in the resulting C-H functionalized triazolopyridine can be readily excised using acidic or oxidative conditions to unmask the pyridine.
- Liu, Sheng,Sawicki, James,Driver, Tom G.
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supporting information; experimental part
p. 3744 - 3747
(2012/08/28)
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- Copper-catalyzed silacarboxylation of internal alkynes by employing carbon dioxide and silylboranes
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Silalactones: The copper-catalyzed reaction of internal alkynes with (dimethylphenylsilyl)pinacolborane (Me2PhSi-B(pin)) as the silicon source and CO2 at atmospheric pressure afforded silalactones selectively in good to high yields. The silalactones can be used as substrates for the Hiyama cross-coupling reaction as demonstrated for one substrate. Copyright
- Fujihara, Tetsuaki,Tani, Yosuke,Semba, Kazuhiko,Terao, Jun,Tsuji, Yasushi
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supporting information
p. 11487 - 11490
(2013/01/15)
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- One-pot carboboration of alkynes using lithium borylcyanocuprate and the subsequent Suzuki-Miyaura cross-coupling of the resulting tetrasubstituted alkenylborane
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We have developed a one-pot carboboration of internal alkynes using lithium borylcyanocuprates 3. Isolation of single crystals of 3·(thf) 3 enabled us to estimate its structural and spectroscopic features. Simple mixing of 3 with ester-substituted alkynes and alkynylarenes was followed by trapping of the resulting intermediate with electrophiles to give tetrasubstituted borylalkenes 4, 5, and 8 in moderate to good yields. Ligand exchange of 8ba from diamine to pinacol allowed us to explore further application of obtained pinacol ester 10ba to subsequent Suzuki-Miyaura cross-coupling reactions to give all-carbon substituted alkene 9ba. Copyright
- Okuno, Yuri,Yamashita, Makoto,Nozaki, Kyoko
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experimental part
p. 3951 - 3958
(2011/09/15)
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- Fritsch-Buttenberg-Wiechell rearrangement to alkynes from gem-dihaloalkenes with lanthanum metal
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The first example of the FBW rearrangement using of lanthanum metal and a catalytic amount of iodine was disclosed. When gem-diiodo- and gem-dibromoalkenes were treated with lanthanum metal in the presence of a catalytic amount of iodine, the reductive dehalogenation of these compounds smoothly proceeded to produce the corresponding alkynes in moderate to good yields.
- Umeda, Rui,Yuasa, Takumi,Anahara, Namika,Nishiyama, Yutaka
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supporting information; experimental part
p. 1916 - 1919
(2011/05/14)
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- Complete study of the pyrolysis and gasification of scrap tires in a pilot plant reactor
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The pyrolysis and gasification of tires was investigated in a pilot plant reactor provided with a system for condensation of semivolatile matter. The study comprised experiments at 450°, 750°, and 1000°C both in nitrogen and 10% oxygen atmospheres. In the gas phase, only methane and benzene yields increased with temperature until 1000°C. In the liquids, the main components were styrene, limonene, and isoprene. The solid fraction (including soot) increased with temperature. Zinc content of the char decreased with increasing temperature. Analysis of the surface area of the solids showed that the area was similar in all cases to that of a commercial carbon black. The higher surface of the soot with respect to the chars was observed. The results coincided with published findings, i.e., kinetic severity function values would produce 0.2% of methane at 450°C and 4.5% at 750°-1000°C.
- Conesa, Juan A.,Martin-Gullon,Font,Jauhiainen
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p. 3189 - 3194
(2008/12/21)
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- The concerted addition of HBr to aryl alkynes; orthogonal pi bond selectivity
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In a weakly acidic solution, the addition of HBr to 1-phenylprop-1-yne produces predominantly the anti-Markovnikov product. In this paper, we consider five possible explanations for this behavior and conclude that the concerted addition is occurring on the acetylenic π bond orthogonal to the extended aromatic π system. The electronic effect of the distal methyl group and the steric hindrance of the coplanar phenyl ring combine to promote bromide attack at the β carbon. Attack on this π bond is insensitive to the electronic effect of meta and para substituents on the ring but is very (sterically) sensitive toward all ortho substituents.
- Weiss, Hilton M.,Touchette, Kim M.,Angell, Sarah,Khan, Jihan
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p. 2152 - 2156
(2007/10/03)
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- Alkyne metathesis with simple catalyst systems: High yield dimerization of propynylated aromatics; scope and limitations
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High yield dimerization of propynylated benzenes and propynylnaphthalene by a mixture of Mo(CO)6 and 4-chlorophenol at 140 °C in 1,2-dichlorobenzene is reported to give the corresponding disubstituted alkynes. The scope and limitation of the reaction and the influence of substitution pattern and substitution type are discussed. Oxygen or nitrogen carrying substrates metathesize in moderate to good yields and ortho-alkyl substituted examples form the respective tolanes very efficiently.
- Pschirer, Neil Gregory,Bunz, Uwe H. F.
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p. 2481 - 2484
(2007/10/03)
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- Synthesis of mono- and diarylacetylenes
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Arylacetylenes have been synthesized by C-C coupling of lithium acetylide with aryl bromide in the presence of a palladium(0) catalyst.
- Al-Hassan, Mohammed I.
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p. 227 - 229
(2007/10/02)
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- AN EFFICIENT METHOD FOR THE SYNTHESIS OF 1-ARYLALKYNES
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1-Arylalkynes are prepared from propiophenones in good yield via the sequence a) 2 equiv PCl5/Δ b) DBN or Δ and c) Mg metal.
- Engler, Thomas A.,Combrink, Keith D.,Ray, James E.
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p. 1735 - 1744
(2007/10/02)
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- Vinylcations, 39. Zinc Chloride Catalysed Addition of Hydrogen Chloride to Cyclopropylalkynes
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Zinc chloride catalysed addition of hydrogen chloride to 1-cyclopropylalkynes 5a-e (R = CH3, c-C3H5, phenyl, p-tolyl, 4-methoxyphenyl) is studied and the results are compared with those of the addition of HCl/ZnCl2 to several substituted arylalkynes 10a-h.Thus, the alkynes are reacted with HCl/ZnCl2 in dichloromethane and the reaction products are investigated also with respect to their stereochemistry.All alkynes yield predominantly the direkt hydrogen chloride addition products.The 1-cyclopropylalkynes 5a-d give (E)-1-chloro-1-cyclopropyl-1-alkenes 15, and (E)-1-chloro-2-cyclopropyl-1-(4-methoxyphenyl)ethene (16e) is obtained as the major product from 5e (R = 4-CH3OC6H4).Moreover, ring opening to homoallenyl chlorides 19 and, as a side reaction, formation of the ketones 17 and 18 by the addition of water are observed.In a secondary addition reaction, the dichlorides 20 are also obtained by homoallyl rearrangement.The arylalkynes 10a-g react preferentially with formation of (E)-1-aryl-1-chloroalkenes 21.Relative rates are obtained by inter- and intramolecular competition reactions of the alkynes 23 and 5b-e with HCl/ZnCl2 showing the order of stabilization by substituents of the intermediate vinyl cation 2 to be 4-ClC6H4 E2 mechanism.The preferential formation of the addition products E-15, E-16, and E-21 is attributed to a syn-vinyl cation ion pair and to steric approach control of the β-substituents in the vinyl cation intermediate 2.
- Hanack, Michael,Weber, Erhard
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p. 777 - 797
(2007/10/02)
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- Choix des methodes pour la synthese univoque de carbures acetyleniques. Troisieme partie : Arylacetylenes et aryl-1 alcynes-1
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The range of applicability of six syntheses of pure alkynes with one aryl group has been defined; a short review of other possible procedures is included.We have specified the best method to obtain selectively the alkynes Ar-CCH and Ar-CC-R, according to the nature of the substituents of the aryl group and according to the developed structure of the R group.It is thus possible to recommend with the largest probability of success the method to obtain, in homogenous series, alkynes corresponding to still more complicated structures.
- Mesnard, Danielle,Bernadou, Francoise,Miginiac, Leone
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p. 3216 - 3245
(2007/10/02)
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