Co-reporter:Hanyang Bao, Zheng Xu, Degui Wu, Haifeng Zhang, Hongwei Jin, and Yunkui Liu
The Journal of Organic Chemistry 2017 Volume 82(Issue 1) pp:109-118
Publication Date(Web):December 2, 2016
DOI:10.1021/acs.joc.6b02212
A general and efficient protocol for the synthesis of 9,10-phenanthraquinone derivatives has been successfully developed involving a copper(0)/Selectfluor system-promoted oxidative carbon–carbon bond cleavage/annulation of o-aryl chalcones. A variety of substituted 9,10-phenanthraquinones were synthesized in moderate to good yields under mild reaction conditions.
Co-reporter:Jian Zhang, Dongdong Shi, Haifeng Zhang, Zheng Xu, Hanyang Bao, Hongwei Jin, Yunkui Liu
Tetrahedron 2017 Volume 73(Issue 2) pp:154-163
Publication Date(Web):12 January 2017
DOI:10.1016/j.tet.2016.11.069
A mild and efficient protocol for the synthesis of dibenzopyranones and pyrazolobenzopyranones was developed involving a copper(0)/Selectfluor system-catalyzed double CH activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes. Preliminary mechanistic studies suggest that both water and dioxygen act as the oxygen source in the formation of pyranone scaffolds.
Co-reporter:Haifeng Zhang;Dongdong Shi;Shaobo Ren;Hongwei Jin
European Journal of Organic Chemistry 2016 Volume 2016( Issue 24) pp:4224-4229
Publication Date(Web):
DOI:10.1002/ejoc.201600667
A selective gem-dichlorination of isonitriles has been successfully achieved by using (dichloroiodo)benzene as a chlorinating reagent. The reaction gives N-arylcarbonimidic dichlorides in high yields under mild and metal-free conditions. The application of N-arylcarbonimidic dichlorides as synthetic intermediates in the synthesis of 2,2,3,3-tetrachloroaziridine 4, propyl formimidate 5, benzophenone imine 6, and 6-chlorophenanthridine (3a) was also investigated.
Co-reporter:Jian Zhang, Heng Wang, Shaobo Ren, Wei Zhang, and Yunkui Liu
Organic Letters 2015 Volume 17(Issue 12) pp:2920-2923
Publication Date(Web):May 29, 2015
DOI:10.1021/acs.orglett.5b01110
A novel and facile method for the mild construction of fluorinated fluorenones from nonaromatic precursors (1,6-enynes) mediated by a Cu(0)/Selectfluor system has been successfully achieved. Preliminary mechanistic investigations indicate that the reaction may proceed via an unprecedented annulation/C–C single bond cleavage/fluorination sequence.
Co-reporter:Shaobo Ren;Jian Zhang;Jiahui Zhang;Heng Wang;Wei Zhang;Miaochang Liu
European Journal of Organic Chemistry 2015 Volume 2015( Issue 24) pp:5381-5388
Publication Date(Web):
DOI:10.1002/ejoc.201500610
Abstract
A route to β-substituted cyclohex-2-enones, 4-arylcoumarins, and biaryls has been developed. This approach involves a one-pot Cu0/Selectfluor-catalyzed dehydration–oxidation of tertiary cycloalcohols. Thus, by using 2 equiv. of Selectfluor at 25 °C, the dehydration–oxidation of tertiary cyclohexanols and oxabenzocyclohexanols gave β-substituted cyclohex-2-enones and 4-arylcoumarins, respectively; whereas the dehydration–oxidation of tertiary cyclohexanols gave biaryls as the final products by using 2.5 equiv. of Selectfluor at 80 °C.
Co-reporter:Heng Wang, Shaobo Ren, Jian Zhang, Wei Zhang, and Yunkui Liu
The Journal of Organic Chemistry 2015 Volume 80(Issue 13) pp:6856-6863
Publication Date(Web):June 7, 2015
DOI:10.1021/acs.joc.5b00857
Selectfluor-mediated simultaneous cleavage of C–O and C–C bonds in α,β-epoxy ketones has been successfully achieved under transition-metal-free conditions. The reaction gives 1,2-diketone compounds in moderate to good yields involving a ring-opening/benzoyl rearrangement/C–C bond cleavage sequence under oxidative conditions.
Co-reporter:Wei Zhang, Shaobo Ren, Jian Zhang, and Yunkui Liu
The Journal of Organic Chemistry 2015 Volume 80(Issue 11) pp:5973-5978
Publication Date(Web):May 20, 2015
DOI:10.1021/acs.joc.5b00735
Palladium-catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate to excellent yields has been developed involving an sp3 C–H bond activation. The resulting (nitromethyl)quinolines could be selectively reduced to (1,2,3,4-tetrahydroquinolin-8-yl)methanamines by NaBH4 in the presence of a catalytic amount of NiCl2·6H2O.
Co-reporter:Degui Wu, Jian Zhang, Jianhai Cui, Wei Zhang and Yunkui Liu
Chemical Communications 2014 vol. 50(Issue 74) pp:10857-10860
Publication Date(Web):25 Jul 2014
DOI:10.1039/C4CC01327A
A unique method for AgNO2-mediated direct nitration of the quinoxaline tertiary C–H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed. This protocol provides an efficient way to access quinoxaline containing nitroalkanes and nitriles depending on different substrate selection.
Co-reporter:Wei Zhang;Degui Wu;Jian Zhang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 26) pp:5827-5835
Publication Date(Web):
DOI:10.1002/ejoc.201402451
Abstract
A regiospecific synthesis of substituted 2-nitrobenzaldehydes from substituted benzaldehydes has been developed that involves a three-step process with palladium-catalyzed chelation-assisted C–H nitration as the key step. In the process, O-methyl aldoxime serves as a removable directing group for the palladium-catalyzed ortho-nitration of substituted benzaldoximes and it can be removed in subsequent conversion of the resulting 2-nitrobenzaldoximes into 2-nitrobenzaldehydes.
Co-reporter:Degui Wu;Jian Zhang;Heng Wang;Jiahui Zhang;Dr. Yunkui Liu; Miaochang Liu
Asian Journal of Organic Chemistry 2014 Volume 3( Issue 11) pp:1163-1167
Publication Date(Web):
DOI:10.1002/ajoc.201402171
Abstract
Activation of dioxygen in air by a combined phenol/Selectfluor system has been revealed. This technique has been exploited to develop an approach to 2-ene-1,4-diones via an oxidation-dimerization of alkynes under metal-free conditions.
Co-reporter:Wei Zhang, Jian Zhang, Shaobo Ren, and Yunkui Liu
The Journal of Organic Chemistry 2014 Volume 79(Issue 23) pp:11508-11516
Publication Date(Web):November 7, 2014
DOI:10.1021/jo502145v
A general and regiospecific transformation of substituted phenols into the related o-nitrophenols has been achieved via a three-step process involving the palladium-catalyzed chelation-assisted ortho-C–H bond nitration as the key step. In the process, 2-pyridinyloxy groups act as removable directing groups for the palladium-catalyzed ortho-nitration of substituted 2-phenoxypridines, and they can be readily removed in the subsequent conversion of the resulting 2-(2-nitrophenoxy)pyridines into 2-nitrophenols.
Co-reporter:Jian Zhang, Degui Wu, Xiaoling Chen, Yunkui Liu, and Zhenyuan Xu
The Journal of Organic Chemistry 2014 Volume 79(Issue 11) pp:4799-4808
Publication Date(Web):May 7, 2014
DOI:10.1021/jo500948b
A Cu(0)/Selectfluor system-mediated oxidative cyclization of 1,5-enynes with concomitant C–C bond cleavage to access 3-formyl-1-indenone derivatives is described. Preliminary mechanistic investigations disclosed that the C–C bond cleavage involved a novel water-participated oxygen-insertion β-carbon elimination through double oxycuprations.
Co-reporter:Wei Zhang, Shaojie Lou, Yunkui Liu, and Zhenyuan Xu
The Journal of Organic Chemistry 2013 Volume 78(Issue 12) pp:5932-5948
Publication Date(Web):May 20, 2013
DOI:10.1021/jo400594j
A palladium-catalyzed chelation-assisted ortho-nitration of aryl C–H bond is described. A range of azaarenes such as 2-arylquinoxalines, pyridines, quinoline, and pyrazoles were nitrated with excellent chemo- and regioselectivity. Using the O-methyl oximyl group as a removable directing group, the regiospecific synthesis of a variety of o-nitro aryl ketones was achieved starting from aryl ketones via a three-step process involving the Pd-catalyzed ipso-nitration of C–H bond as a key step. Mechanistic investigations support a silver-mediated radical mechanism involving Pd((II/III) and/or Pd(II/IV) catalytic cycles under oxidizing conditions.
Co-reporter:Yunkui Liu, Bo Jiang, Wei Zhang, and Zhenyuan Xu
The Journal of Organic Chemistry 2013 Volume 78(Issue 3) pp:966-980
Publication Date(Web):January 7, 2013
DOI:10.1021/jo302450f
A K2S2O8-mediated direct cross-coupling of quinoxalines (or benzothiazoles) with methanol leading to 2-quinoxalinyl (or 2-benzothiazolyl) carbaldehyde dimethyl acetals has been achieved. 2-Quinoxalinyl carbaldehyde dimethyl acetals were readily converted into 2-quinoxalinyl carbaldehydes in good to excellent yields under acidic conditions. Preliminary mechanistic studies suggest that the reaction proceeds via multifold bond cleavage and formation between methanol and N-heterocycles involving a dioxygen-participated radical process. This method allows for the synthesis of a variety of 2-quinoxalinyl (or 2-benzothiazolyl) carbaldehyde dimethyl acetals directly via cross-coupling of simple N-heterocyclic C–H bond and methanol under aldehyde-, acid-, and transition-metal-free conditions.
Co-reporter:Yunkui Liu, Jie Zhu, Jianqiang Qian, and Zhenyuan Xu
The Journal of Organic Chemistry 2012 Volume 77(Issue 12) pp:5411-5417
Publication Date(Web):May 30, 2012
DOI:10.1021/jo3006528
An approach for the synthesis of fluorinated indene derivatives has been developed via a gold-catalyzed three-component tandem reaction between allene esters, Selectfluor, and water.
Co-reporter:Jianqiang Qian, Yunkui Liu, Jianhai Cui, and Zhenyuan Xu
The Journal of Organic Chemistry 2012 Volume 77(Issue 9) pp:4484-4490
Publication Date(Web):April 17, 2012
DOI:10.1021/jo300543n
A unique gold(I)-catalyzed highly atom-economic synthesis of 1,5-benzodiazepines directly from o-phenylenediamines and alkynes has been achieved for the first time.
Co-reporter:Yunkui Liu, Jie Zhu, Jianqiang Qian, Bo Jiang, and Zhenyuan Xu
The Journal of Organic Chemistry 2011 Volume 76(Issue 21) pp:9096-9101
Publication Date(Web):September 27, 2011
DOI:10.1021/jo201342m
An efficient and selective approach for the synthesis of functionalized pyranocoumarins has been developed via a gold(III)-catalyzed tandem conjugate addition/annulation reaction of 4-hydroxycoumarins with α,β-unsaturated ketones.
Co-reporter:Dr. Yun-Kui Liu;Dr. Shao-Jie Lou;Dr. Dan-Qian Xu ;Zhen-Yuan Xu
Chemistry - A European Journal 2010 Volume 16( Issue 46) pp:13590-13593
Publication Date(Web):
DOI:10.1002/chem.201002581
Co-reporter:Degui Wu, Jian Zhang, Jianhai Cui, Wei Zhang and Yunkui Liu
Chemical Communications 2014 - vol. 50(Issue 74) pp:NaN10860-10860
Publication Date(Web):2014/07/25
DOI:10.1039/C4CC01327A
A unique method for AgNO2-mediated direct nitration of the quinoxaline tertiary C–H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed. This protocol provides an efficient way to access quinoxaline containing nitroalkanes and nitriles depending on different substrate selection.