Co-reporter:Xin-Qi Hao, Ya-Nan Dong, Biao Gao, Ke Li, Xue-Mei Zhao, Yan Xu, Mao-Ping Song
Tetrahedron: Asymmetry 2015 Volume 26(Issue 23) pp:1360-1368
Publication Date(Web):15 December 2015
DOI:10.1016/j.tetasy.2015.10.007
Co-reporter:Xinqi Hao, Chaoli Liu, Chenli Liu, Yiyong Chen, Xuemei Zhao, Maoping Song, Rong Qian, Hao Guo
Tetrahedron Letters 2013 Volume 54(Issue 50) pp:6964-6966
Publication Date(Web):11 December 2013
DOI:10.1016/j.tetlet.2013.10.063
THF is found to react with aromatic aldehydes or ketones highly chemoselectively under the irradiation of ultraviolet without any additives, which provides a new protocol to access α-di or trisubstituted (tetrahydrofuran-2-yl)methanols. The scope of this reaction is well studied.THF is found to react with aromatic aldehydes or ketones highly chemoselectively under the irradiation of ultraviolet without any additives, which provides a new protocol to access α-di or trisubstituted (tetrahydrofuran-2-yl)methanols. The scope of this reaction is well studied.
Co-reporter:Hong-Mei Li, Chen Xu, Xin-Qi Hao, Zhen Li, Zhi-Qiang Wang, Wei-Jun Fu, Mao-Ping Song
Inorganica Chimica Acta 2013 Volume 404() pp:236-240
Publication Date(Web):1 August 2013
DOI:10.1016/j.ica.2013.04.014
•Synthesis of substituted biarylmethanol by the Suzuki reaction in water.•Cationic palladacycle 2 has been synthesized and characterized.•2 was an efficient catalyst for the Suzuki reaction in water.A new cationic cyclopalladated ferrocenylpyrimidine 2 has been synthesized and characterized by elemental analysis, IR, 1H and C13 NMR. Additionally, its detailed structure has been determined by single-crystal X-ray diffraction and intermolecular C–H⋯O hydrogen bonds were found in the its crystal. 2 was successfully used in Suzuki reaction of aryl bromides or chlorides excluding water-soluble group with 4-(hydroxymethyl)phenylboronic acid for the synthesis of substituted biarylmethanol in water. Complex 2 was found to be very efficient for these reactions. Typically, using 0.5–1 mol% of catalyst in the presence of 3 equivalents of K3PO4·3H2O as base in water at 100 °C provided coupling products in good yields.A new cationic palladacycle 2 has been synthesized and characterized. Its detailed structure has been determined by single-crystal X-ray analysis. 2 was found to be efficient catalyst for the Suzuki reactions of aryl bromides or chlorides excluding water-soluble group with 4-(hydroxymethyl)phenylboronic acid in water. This procedure represents a practical method for the synthesis of substituted biarylmethanol.
Co-reporter:Chen Xu, Xin-Qi Hao, Zhi-Qiang Xiao, Zhi-Qiang Wang, Xiao-Er Yuan, Wei-Jun Fu, Bao-Ming Ji, and Mao-Ping Song
The Journal of Organic Chemistry 2013 Volume 78(Issue 17) pp:8730-8738
Publication Date(Web):August 7, 2013
DOI:10.1021/jo401421b
An efficient PPh3-cyclometalated iridium(III) benzo[h]quinoline hydride 1/Pd(OAc)2-cocatalyzed three-component α-alkylation/Suzuki reaction has been developed. The three-component reaction of 4-bromobenzyl alcohol, acetylferrocene, and arylboronic acids gives ferrocenyl ketones containing biaryls in moderate to good yields. This method was successfully applied to a one-pot synthesis of 6-aryl-2-ferrocenyl quinolines, using (2-amino-5-bromophenyl)methanol instead of 4-bromobenzyl alcohol.
Co-reporter:Chen Xu, Xin-Qi Hao, Zhen Li, Xin-Ming Dong, Lu-Meng Duan, Zhi-Qiang Wang, Bao-Ming Ji, Mao-Ping Song
Inorganic Chemistry Communications 2012 Volume 17() pp:34-37
Publication Date(Web):March 2012
DOI:10.1016/j.inoche.2011.12.009
Two new N-heterocyclic carbene (NHC)-phosphine palladium(II) complexes Pd(IMeo)PPh3I21 and Pd(IMeo) P(C6H4-p-Me)3I22 (IMeo = 1,3-di-4-methoxyphenyl- imidazolin-2-ylidene) have been easily prepared from the reaction of the corresponding iodide-bridged NHC dimer with phosphine ligands in high yields. Complexes 1 and 2 were characterized by elemental analysis, IR, 1H NMR, ESI-MS and single-crystal X-ray analysis. Complex 1 adopts a trans geometry in the solid state, while 2 is cis. The common features of the structures of these complexes are intermolecular CH⋯I and CH⋯O hydrogen bonds. These complexes were found to be efficient catalysts for the Suzuki reaction of aryl bromides.Two new N-heterocyclic carbene–phosphine palladium(II) complexes 1 and 2 have been synthesized. Complex 1 adopts a trans geometry in the solid state, while 2 is cis. These complexes were found to be efficient catalysts for the Suzuki reaction of aryl bromides.Highlights► Two NHC-phosphine palladium(II) complexes have been synthesized. ► Complex 1 adopts a trans geometry in the solid state, while 2 is cis. ► The two complexes were effective catalysts for the Suzuki reaction.
Co-reporter:Chen Xu, Zhi-Qiang Wang, Zhen Li, Wei-Zhou Wang, Xin-Qi Hao, Wei-Jun Fu, Jun-Fang Gong, Bao-Ming Ji, and Mao-Ping Song
Organometallics 2012 Volume 31(Issue 3) pp:798-801
Publication Date(Web):January 23, 2012
DOI:10.1021/om201267q
The 1,3-diphosphorus ylide cyclopentadienylium salts (C5H3)(PPh3)2I (1) and (C5H3)[P(4-CH3-Ph)3]2I (2) have been prepared from the reaction of 1,1′-dichloromercurioferrocene with Pd(PPh3)4 and with Pd[P(4-CH3-Ph)3]4, respectively. The molecular structure of 1 has been determined by X-ray diffraction analyses. The Pd(OAc)2/1 or 2/KtOBu system is highly efficient for the coupling reactions of aryl chlorides at room temperature.
Co-reporter:Xue-Mei Zhao;Xin-Qi Hao;Kun-Lun Wang;Jun-Rui Liu
Transition Metal Chemistry 2009 Volume 34( Issue 6) pp:683-688
Publication Date(Web):2009 September
DOI:10.1007/s11243-009-9248-2
Catalytic studies on the air- and moisture-stable triphenylphosphine (PPh3) adducts of heteroannular cyclopalladated ferrocenylimines [PdCl{C5H4FeC5H4CHRN=CHC4H3X}(Ph3P)] (R = H, CH3; X = S, O) indicate that they are all effective catalysts for the Suzuki–Miyaura coupling reaction of activated aryl bromides with phenylboronic acid in water under air atmosphere. Typically, using 1 mol‰ of catalyst in the presence of 1.2 equivalents of K3PO4 as base in water at 100 °C provided the corresponding biaryls in good to excellent yields. Meanwhile, the structure of [PdCl{C5H4FeC5H4CH(CH3)N=CHC4H3S}(PPh3)] has been established by the single-crystal X-ray diffraction technique. According to the crystal structure, the palladium atom is bound to the unsubstituted Cp ring, showing the four-coordinate structure typical of palladium complexes.
Co-reporter:Wei Liu, Maolin Zhang, Xia Li, Maoping Song
Inorganic Chemistry Communications 2008 Volume 11(Issue 6) pp:694-698
Publication Date(Web):June 2008
DOI:10.1016/j.inoche.2008.01.013
A simple and efficient one-pot synthetic methodology for the preparation of 1,1′-ferrocenediylbis-(methyltriphenylphosphonium iodide) is described. And the obtained salt has been used for the construction of ferrocene-containing pyridine ligands 3a–b. Electrochemical investigations of 3a–b have demonstrated that upon addition of Hg2+ and Zn2+ results in large shifts of respective Fc/Fc+ redox couple to more positive potentials. Titration experiment shows that the current associated with the new redox couple increases linearly with the concentration of Hg2+ until a full equivalent has been added, which suggests that 3b is a good candidate for an amperometric sensor to detect the toxic Hg2+.A simple and efficient one-pot synthetic methodology for the preparation of 1,1′-ferrocenediylbis-(methyltriphenylphosphonium iodide) is described. And the obtained salt has been used for the construction of ferrocene-containing pyridine ligands 3a–b. Electrochemical investigations of 3a–b have demonstrated that upon addition of Hg2+ and Zn2+ results in large shifts of respective Fc/Fc+ redox couple to more positive potentials. Titration experiment shows that the current associated with the new redox couple increases linearly with the concentration of Hg2+ until a full equivalent has been added, which suggests that 3b is a good candidate for an amperometric sensor to detect the toxic Hg2+.