Co-reporter:Jin Huang, Wei Wang, Hai-Yu He, Lei Jian, Hai-Yan Fu, Xue-Li Zheng, Hua Chen, and Rui-Xiang Li
The Journal of Organic Chemistry 2017 Volume 82(Issue 5) pp:
Publication Date(Web):February 6, 2017
DOI:10.1021/acs.joc.6b02902
A simple and efficient strategy for the synthesis of 1-propenylnaphthols from readily accessible 3-arylallylnaphthyl ethers has been developed. By using K2CO3 as base and 2-methoxyethanol as solvent, direct access to a wide range of 1-propenylnaphthols can be achieved in generally good yield (up to 99%) with high stereoselectivity toward the Z isomer. The control experiments indicate that the reaction proceeds through a sequential Claisen rearrangement/isomerization process. Furthermore, starting from the same material, the highly valuable 3-arylnaphtho[2,1-b]furans can be obtained in N,N-dimethylformamide and in the presence of Ag2O as the oxidant via a one-pot sequential Claisen rearrangement/isomerization/cyclization reaction. Mechanistic studies confirm that 1-propenylnaphthols are the key intermediates to form the 3-arylnaphtho[2,1-b]furans. In addition, these two operationally simple and practical protocols could be scaled up to a gram level.
Co-reporter:Lei Jian;Hai-Yu He;Jin Huang;Qian-Hui Wu;Mao-Lin Yuan;Hai-Yan Fu;Xue-Li Zheng;Hua Chen;Rui-Xiang Li
RSC Advances (2011-Present) 2017 vol. 7(Issue 38) pp:23515-23522
Publication Date(Web):2017/04/27
DOI:10.1039/C7RA02638B
A simple and recyclable catalytic system for direct arylation of heteroarenes via C–H bond activation was developed with a relatively inexpensive RuCl3·xH2O as a catalyst and PEG-400 as a green medium without any additive or ligand. This system not only showed excellent functional group compatibility, but also the ratio of mono- to diarylated product was easily regulated by varying the reaction conditions. Moreover, this transformation could proceed under air and be easily scaled up to gram-scale in a low catalyst loading of 0.3 mol%. Particularly, a good yield of 85% was obtained after this catalyst was recycled six times.
Co-reporter:Lei Jian;Hai-Yu He;Jin Huang;Qian-Hui Wu;Mao-Lin Yuan;Hai-Yan Fu;Xue-Li Zheng;Hua Chen;Rui-Xiang Li
RSC Advances (2011-Present) 2017 vol. 7(Issue 38) pp:23515-23522
Publication Date(Web):2017/04/27
DOI:10.1039/C7RA02638B
A simple and recyclable catalytic system for direct arylation of heteroarenes via C–H bond activation was developed with a relatively inexpensive RuCl3·xH2O as a catalyst and PEG-400 as a green medium without any additive or ligand. This system not only showed excellent functional group compatibility, but also the ratio of mono- to diarylated product was easily regulated by varying the reaction conditions. Moreover, this transformation could proceed under air and be easily scaled up to gram-scale in a low catalyst loading of 0.3 mol%. Particularly, a good yield of 85% was obtained after this catalyst was recycled six times.
Co-reporter:Wei Wang;Jin Huang;Rong Zhou;Zhi-Jie Jiang;Hai-Yan Fu;Xue-Li Zheng;Hua Chen;Rui-Xiang Li
Advanced Synthesis & Catalysis 2015 Volume 357( Issue 11) pp:2442-2446
Publication Date(Web):
DOI:10.1002/adsc.201500151
Co-reporter:Wei Wang;Rong Zhou;Zhi-Jie Jiang;Xin Wang;Hai-Yan Fu;Xue-Li Zheng;Hua Chen ;Rui-Xiang Li
European Journal of Organic Chemistry 2015 Volume 2015( Issue 12) pp:2579-2584
Publication Date(Web):
DOI:10.1002/ejoc.201500116
Abstract
A palladium-catalyzed domino Mizoroki–Heck/intermolecular unactivated C(sp3)–H alkylation reaction has been developed. This simple palladium nanoparticle catalytic system shows good activity and affords the dimeric dihydrobenzofuran derivatives in moderate to good yields. Furthermore, this reaction provides a new method for the elaboration of domino reactions involving a C(sp3)–C(sp3) bond-forming process.
Co-reporter:Rong Zhou, Wei Wang, Zhi-jie Jiang, Kun Wang, Xue-li Zheng, Hai-yan Fu, Hua Chen and Rui-xiang Li
Chemical Communications 2014 vol. 50(Issue 45) pp:6023-6026
Publication Date(Web):14 Apr 2014
DOI:10.1039/C4CC00815D
A catalyst composed of [Pd(η3-C3H5)Cl]2 and N,N,N',N'-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine (L) was found to be effective for one-pot synthesis of 2-substituted benzo[b]furans from 2-halophenols and alkynes. For 2-bromo-3-hydroxypyridine, the catalyst loading could be as low as 1 ppm and the turnover number (TON) was up to 870000.
Co-reporter:Wei Wang;Rong Zhou;Zhi-Jie Jiang;Kun Wang;Hai-Yan Fu;Xue-Li Zheng;Hua Chen ;Rui-Xiang Li
Advanced Synthesis & Catalysis 2014 Volume 356( Issue 2-3) pp:616-622
Publication Date(Web):
DOI:10.1002/adsc.201300757
Co-reporter:Lei Zhang, Xiaoyan Wang, Ying Xue, Xiaojun Zeng, Hua Chen, Ruixiang Li and Shanling Wang
Catalysis Science & Technology 2014 vol. 4(Issue 7) pp:1939-1948
Publication Date(Web):15 Jan 2014
DOI:10.1039/C3CY01071F
A well dispersed core–shell nanocatalyst, Ru–SiO2@mSiO2, with a Brunauer–Emmet–Teller surface area (SBET) as high as 602 m2 g−1, has been prepared by a modified Stöber method and characterized by SEM, TEM, SAXRD and solid-state NMR. The catalyst shows a good catalytic performance for the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline under mild conditions in water. Both the conversion and selectivity are up to 100%. Furthermore, the catalyst could be recycled up to five times without loss of both the activity and selectivity. It is postulated that the high performance of this novel catalytic system is related to the cooperation between the surface hydroxyl groups of the microporous shell of Ru–SiO2@mSiO2 and water as a solvent.
Co-reporter:Rong Zhou, Wei Wang, Zhi-jie Jiang, Hai-yan Fu, Xue-li Zheng, Chun-chun Zhang, Hua Chen and Rui-xiang Li
Catalysis Science & Technology 2014 vol. 4(Issue 3) pp:746-751
Publication Date(Web):22 Nov 2013
DOI:10.1039/C3CY00831B
An efficient copper-free Sonogashira coupling reaction was performed on water at 100 °C with N,N,N′,N′-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine (1) as a ligand, [Pd(η3-C3H5)Cl]2 as a catalyst precursor and K3PO4 as a base. Both aryl and heteroaryl halides were successfully alkynylated in this system, and a high turnover number (TON) up to 860000 was obtained with a catalyst loading as low as 1 ppm.
Co-reporter:Zhu Zhu, Jie Zhang, Haiyan Fu, Maolin Yuan, Xueli Zheng, Hua Chen and Ruixiang Li
RSC Advances 2014 vol. 4(Issue 95) pp:52734-52739
Publication Date(Web):07 Oct 2014
DOI:10.1039/C4RA07524B
Convenient synthesis of four new distorted octahedral ruthenium(II) complexes (1, 2, 3, 4) having general molecular formula [RuCl2LPAr3] (L = pyridine-based tridentate ligands not containing N–H bonds) is described. Their composition and structure were determined by elemental analysis and NMR spectra, and complexes 2 and 4 were also identified by X-ray single-crystal diffraction. All ruthenium(II) complexes exhibited good to excellent catalytic activity in the transfer hydrogenation of ketones. Among them, complex 4 achieved the highest final TOF value of 51600 h−1 for a high molar ratio of substrate to catalyst (2000:1).
Co-reporter:Deming Zhu;Hongbin Jiang;Lei Zhang;Xueli Zheng;Haiyan Fu;Maolin Yuan; Hua Chen ; Ruixiang Li
ChemCatChem 2014 Volume 6( Issue 10) pp:2954-2960
Publication Date(Web):
DOI:10.1002/cctc.201402519
Abstract
A new ruthenium catalyst supported on glucose-derived carbon spheres was prepared by using the impregnation method and then characterized by X-ray photoelectron spectroscopy, XRD, TEM, SEM, FTIR, and solid-state 13C MAS NMR techniques. With water as the environmentally friendly solvent, the conversion of quinoline and the selectivity toward decahydroquinoline could reach 98.2 and 95.2 %, respectively, under mild conditions (reaction temperature=393 K and H2 pressure=2.0 MPa). The catalyst could be recycled thrice without decrease in activity and selectivity. The excellent catalytic performance of this catalyst may be attributed to the hydrogen bond between the hydroxyl group of the support surface and the nitrogen atom in quinoline as well as to the π–π interaction between the organic support and quinoline.
Co-reporter:Juan Wei;Xiaomin Zhang;Xiaoming Zhang;Yaopeng Zhao; Ruixiang Li; Qihua Yang
ChemCatChem 2014 Volume 6( Issue 5) pp:1368-1374
Publication Date(Web):
DOI:10.1002/cctc.201301011
Abstract
The polymer–inorganic hybrid core–shell nanospheres with N-(para-toluenesulfonyl)-1,2-diphenylethylenediamine in the core and the poly(methyl acrylate) (PMA) polymer in the shell were prepared by using a sol–gel process. The surface properties of solid catalysts were modified by controlling PMA and the cetyltrimethylammonium bromide surfactant in the shell. The water contact angle results suggest that the presence of PMA and cetyltrimethylammonium bromide in the shell increases the surface hydrophobicity. In the Rh-catalyzed transfer hydrogenation of aromatic ketones in aqueous HCOONa, the solid catalyst with higher surface hydrophobicity demonstrates higher activity, which suggests that suitable surface properties increase the reaction rate by increasing the diffusion rates of hydrophobic substrates. Furthermore, this heterogeneous catalyst can be reused conveniently without loss of ee values.
Co-reporter:Juan Wei;Xiaoming Zhang;Yaopeng Zhao
Macromolecular Chemistry and Physics 2013 Volume 214( Issue 19) pp:2232-2238
Publication Date(Web):
DOI:10.1002/macp.201300321
Co-reporter:Qi Fu, Lei Zhang, Tao Yi, Mingjun Zou, Xiaoyan Wang, Haiyan Fu, Ruixiang Li, Hua Chen
Inorganic Chemistry Communications 2013 Volume 38() pp:28-32
Publication Date(Web):December 2013
DOI:10.1016/j.inoche.2013.10.013
Highlights•Two new Ru-phosphine complexes were prepared.•The structure of complex 1 was confirmed by X-ray crystallography.•Both complexes showed good catalytic activities in the transfer hydrogenation.The new ruthenium (II) phosphine complexes (η6-C6H6)RuCl2[μ- (PPh2CH2N)2CH2(C10H6)]RuCl2(η6-C6H6) (1) and RuCl2(PPh3)[(PPh2CH2N)2CH2(C10H6)] (2) were synthesized and characterized by 1H NMR, 31P {1H} NMR and elemental analysis. Moreover, the structure of ruthenium (II) phosphine complex 1 was confirmed by X-ray crystallography. With complex 1 as the catalyst, the transfer hydrogenation of ketones reacted well, affording the corresponding alcohols in good yields under mild conditions.The new ruthenium (II) complexes based on a phosphine ligand 1,3-bis[(diphenylphosphanyl)methyl]-2,3-dihydro-1H-perimidine were synthesized and characterized. Both are valuable for the transfer hydrogenation of aromatic ketones.
Co-reporter:Kun Wang;Qi Fu;Rong Zhou;Xueli Zheng;Haiyan Fu;Hua Chen
Applied Organometallic Chemistry 2013 Volume 27( Issue 4) pp:232-238
Publication Date(Web):
DOI:10.1002/aoc.2965
An easily prepared tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (L1) associated with [Pd(η3-C3H5)Cl]2 affords an efficient catalyst for Suzuki–Miyaura coupling of 3-pyridineboronic acid with heteroaryl bromides. Reaction could be performed with as little as 0.02 mol% catalyst and a high turnover number of 2500 is obtained. A wide range of substrates is investigated with satisfactory yields, and good compatibility with aminogroup-substituted pyridines and unprotected indole is exhibited. This protocol can also be applied successfully to the reaction of heteroaryl bromides with 3-thiopheneboronic acid. This Pd-tetraphosphine catalyst efficiently restrains the poisoning effect from heteroaryls, and shows good stability and longevity. Copyright © 2013 John Wiley & Sons, Ltd.
Co-reporter:Kun Wang;Wei Wang;Heng Luo;Xueli Zheng;Haiyan Fu;Hua Chen
Catalysis Letters 2013 Volume 143( Issue 11) pp:1214-1219
Publication Date(Web):2013 November
DOI:10.1007/s10562-013-1028-0
An air-stable tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-benzene-1,3-diamine (L3) was easily prepared in two steps from triphenylphosphine, which in combination with [Pd(η3-C3H5)Cl]2 affords an efficient catalyst for Suzuki–Miyaura coupling of activated chloroarenes. Even at high temperature of 130 °C, this catalyst exhibits good stability and longevity, and could allow a high turnover number of 680,000 to be reached.
Co-reporter:Jie Zhang;Qin Yang;Zhu Zhu;Mao Lin Yuan;Hai Yan Fu;Xue Li Zheng;Hua Chen ;Rui Xiang Li
European Journal of Organic Chemistry 2012 Volume 2012( Issue 34) pp:6702-6706
Publication Date(Web):
DOI:10.1002/ejoc.201201127
Abstract
A simple and highly efficient method for the cross-coupling of aromatics by C–H activation is described. Acetamide was found to be an effective cocatalyst for this generally applicable ruthenium(II)-catalyzed direct arylation reaction. A wide range of deactivated aryl chlorides could be efficiently coupled under the mild temperature of 101 °C. The new process is highly atom-economical and sustainable.
Co-reporter:Kun Wang;Tao Yi;Xiaojun Yu;Xueli Zheng;Haiyan Fu;Hua Chen
Applied Organometallic Chemistry 2012 Volume 26( Issue 7) pp:342-346
Publication Date(Web):
DOI:10.1002/aoc.2869
An easily prepared tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (1) combined with PdCl2 affords an efficient catalytic system for Suzuki cross-coupling of aryl and heteroaryl bromides. A high turnover number of 750 000 is obtained with the catalyst loading as low as 1 ppm. This catalyst system exhibits good stability and longevity. In this study, a broad scope of substrates is investigated and satisfactory yields are obtained. Copyright © 2012 John Wiley & Sons, Ltd.
Co-reporter:Wei Wang, Qin Yang, Rong Zhou, Hai-Yan Fu, Rui-Xiang Li, Hua Chen, Xian-Jun Li
Journal of Organometallic Chemistry 2012 697(1) pp: 1-5
Publication Date(Web):
DOI:10.1016/j.jorganchem.2011.10.002
Co-reporter:Tao Yi;Min Mo;Hai-Yan Fu;Rui-Xiang Li;Hua Chen;Xian-Jun Li
Catalysis Letters 2012 Volume 142( Issue 5) pp:594-600
Publication Date(Web):2012 May
DOI:10.1007/s10562-012-0796-2
In this study, an easily synthesized polydentate ligand N,N,N’,N’-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (1) in combination with [Pd(C3H5)Cl]2 was found to be an active catalyst in copper-free Sonogashira reactions. Most substrates, including steric hindered phenyl bromides and heteroaryl bromides, could couple efficiently with terminal alkynes in the presence of low catalyst loading (0.1 mol%) and this catalytic system showed excellent functional group tolerance. The influence of water in this system was also preliminarily investigated via 31P NMR in situ; that is, appropriate water favors the reaction while excess hindered this reaction.
Co-reporter:Lei Wang;Qin Yang;Hai-Yan Fu;Hua Chen;Mao-Lin Yuan ;Rui-Xiang Li
Applied Organometallic Chemistry 2011 Volume 25( Issue 8) pp:626-631
Publication Date(Web):
DOI:10.1002/aoc.1818
Abstract
Three Ru–η6-benzene–phosphine complexes bearing tri-(p-methoxyphenyl)phosphine, triphenylphosphine and tri-(p-trifluoromethylphenyl)phosphine were synthesized and characterized by 31P{1H} NMR, 1H NMR, 13C{1H} NMR and elemental analyses. Complex 1 was further identified by X-ray crystallography. These complexes exhibit good to excellent activities for the transfer hydrogenation of ketones in refluxing 2-propanol, and the highest turnover frequency (TOF) is up to 5940 h−1. The effect of electronic factors of these complexes on the transfer hydrogenation of ketones reveals that the catalytic activity is promoted by electron-donating phosphine and the catalyst stability is improved by electron-withdrawing phosphine. Copyright © 2011 John Wiley & Sons, Ltd.
Co-reporter:Lei Wang, Qin Yang, Hua Chen, Rui-Xiang Li
Inorganic Chemistry Communications 2011 Volume 14(Issue 12) pp:1884-1888
Publication Date(Web):December 2011
DOI:10.1016/j.inoche.2011.09.003
A novel cationic dinuclear ruthenium complex [RuCl(HL)(TFTPP)]2 (H2L = 2,6-bis(5-phenyl-1H-pyrazol-3-yl)pyridine; TFTPP = tri(p-trifluoromethylphenyl)phosphine) has been synthesized and characterized by 31P{1H} NMR, 1H NMR, elemental analysis and X-ray crystallography. This complex is the first cationic dinuclear ruthenium complex bearing N4 ligand characterized by single crystal X-ray analysis. It exhibits good catalytic activity for the transfer hydrogenation of ketones in refluxing 2-propanol.A novel cationic dinuclear complex [Ru(HL)(TFTPP)Cl]2 (H2L = 2,6-bis(5-phenyl-1H-pyrazol-3-yl)pyridine; TFTPP = tri(p-trifluoromethylphenyl)phosphine) has been synthesized and it exhibited a good catalytic activity in the transfer hydrogenation of ketones.Highlights► A novel cationic dinuclear ruthenium complex bearing N4 ligand has been synthesized and characterized. ► Complex 1 is the first crystallographic determination of bimetallic Ru complex with N4 ligand. ► Complex 1 is an efficient catalyst in the transfer hydrogenation of ketones, even with 0.02 mol% loading.
Co-reporter:Guangyin Fan;Yafen Zhou;Haiyan Fu;Xiaoli Ye;Hua Chen;Xianjun Li
Chinese Journal of Chemistry 2011 Volume 29( Issue 2) pp:229-236
Publication Date(Web):
DOI:10.1002/cjoc.201190071
Abstract
Hydrous zirconia supported ruthenium catalyst Ru/ZrO2·xH2O, prepared by co-precipitating ruthenium trichloride and zirconium oxychloride with ammonia, was able to catalyze efficiently methyl propionate to propanol under the mild conditions. In aqueous system, the propanol yield of >99% was achieved under the conditions of reaction temperature of 150°C and hydrogen pressure of 5.0 MPa, while in non-aqueous system the maximum propanol yield was only 47.0%. FTIR spectra and hydrogenation results indicated that the high catalytic performance of Ru/ZrO2·xH2O in aqueous phase results from the cooperation effect between water as a solvent and hydroxyl groups on the surface of carrier.
Co-reporter:Fei-chen Guo, Rong Zhou, Zhi-jie Jiang, Wei Wang, Hai-yan Fu, Xue-li Zheng, Hua Chen, Rui-xiang Li
Catalysis Communications (5 June 2015) Volume 66() pp:87-90
Publication Date(Web):5 June 2015
DOI:10.1016/j.catcom.2015.03.028
•TPPDA in combination with PdCl2 was originally used to catalyze Suzuki coupling.•The catalytic system gave a high TON of 3,350,000 for 3-bromochlorobenzene.•For 4-trifluoromethyl-2-nitrochlorobenzene, a TON of 9,900 was obtained.An easily synthesized tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine (TPPDA) in combination with PdCl2 was proved to be a highly efficient catalyst for Suzuki–Miyaura cross-coupling. This system could catalyze a variety of aryl halide substrates with a wide range of functional groups as well as heteroaryl halides. A high turnover number (TON) up to 3,350,000 was reached for 3-bromochlorobenzene.An easily synthesized tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine (TPPDA) in combination with PdCl2 was proved to be a highly efficient catalyst for Suzuki–Miyaura cross-coupling.Download full-size image
Co-reporter:Juan Wei, Hai-Yan Fu, Rui-Xiang Li, Hua Chen, Xian-Jun Li
Catalysis Communications (31 March 2011) Volume 12(Issue 8) pp:748-752
Publication Date(Web):31 March 2011
DOI:10.1016/j.catcom.2011.01.008
A highly efficient system composed of Pd-TPPTS [TPPTS: trisodium salt of tri(m-sulphonylphenyl)phosphine] and halogen-free ionic liquid ([Rmim][p-CH3C6H4SO3], R = methyl, ethyl, n-butyl, n-hexyl, n-octyl, n-dodecyl) has been established for Heck coupling of aryl halides with styrene. Most of the investigated substrates could give the complete conversions (> 95%) with the catalyst of 1 mol% at 110 °C. The resulting products can be easily separated from the ionic liquids by simple liquid-liquid extraction, and the catalyst immobilized by ionic liquids can be consecutively run five times without significant loss in catalytic activity.Water-soluble Pd-TPPTS carried out the highly efficient Mizoroki–Heck coupling of aryl halide with styrene in [Rmim][p-CH3C6H4SO3].Download full-size imageHighlights► Water-soluble ionic liquid [Rmim][p-CH3C6H4SO3] was originally used for Heck coupling. ► The system showed the high reactivity and selectivity with the low palladium loading of 1 mol%. ► Catalyst was recovered easily and recycled.
Co-reporter:Lei Zhang, Xiaoyan Wang, Ying Xue, Xiaojun Zeng, Hua Chen, Ruixiang Li and Shanling Wang
Catalysis Science & Technology (2011-Present) 2014 - vol. 4(Issue 7) pp:NaN1948-1948
Publication Date(Web):2014/01/15
DOI:10.1039/C3CY01071F
A well dispersed core–shell nanocatalyst, Ru–SiO2@mSiO2, with a Brunauer–Emmet–Teller surface area (SBET) as high as 602 m2 g−1, has been prepared by a modified Stöber method and characterized by SEM, TEM, SAXRD and solid-state NMR. The catalyst shows a good catalytic performance for the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline under mild conditions in water. Both the conversion and selectivity are up to 100%. Furthermore, the catalyst could be recycled up to five times without loss of both the activity and selectivity. It is postulated that the high performance of this novel catalytic system is related to the cooperation between the surface hydroxyl groups of the microporous shell of Ru–SiO2@mSiO2 and water as a solvent.
Co-reporter:Rong Zhou, Wei Wang, Zhi-jie Jiang, Hai-yan Fu, Xue-li Zheng, Chun-chun Zhang, Hua Chen and Rui-xiang Li
Catalysis Science & Technology (2011-Present) 2014 - vol. 4(Issue 3) pp:NaN751-751
Publication Date(Web):2013/11/22
DOI:10.1039/C3CY00831B
An efficient copper-free Sonogashira coupling reaction was performed on water at 100 °C with N,N,N′,N′-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine (1) as a ligand, [Pd(η3-C3H5)Cl]2 as a catalyst precursor and K3PO4 as a base. Both aryl and heteroaryl halides were successfully alkynylated in this system, and a high turnover number (TON) up to 860000 was obtained with a catalyst loading as low as 1 ppm.
Co-reporter:Rong Zhou, Wei Wang, Zhi-jie Jiang, Kun Wang, Xue-li Zheng, Hai-yan Fu, Hua Chen and Rui-xiang Li
Chemical Communications 2014 - vol. 50(Issue 45) pp:NaN6026-6026
Publication Date(Web):2014/04/14
DOI:10.1039/C4CC00815D
A catalyst composed of [Pd(η3-C3H5)Cl]2 and N,N,N',N'-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine (L) was found to be effective for one-pot synthesis of 2-substituted benzo[b]furans from 2-halophenols and alkynes. For 2-bromo-3-hydroxypyridine, the catalyst loading could be as low as 1 ppm and the turnover number (TON) was up to 870000.