Co-reporter:Yan Li, Xiaohuan Jiang, Chaoyue Zhao, Xiaoning Fu, Xiufang Xu, and Pingping Tang
ACS Catalysis March 3, 2017 Volume 7(Issue 3) pp:1606-1606
Publication Date(Web):January 25, 2017
DOI:10.1021/acscatal.6b03529
A silver-catalyzed radical hydroxyfluorination of styrenes with Selectfluor and H2O has been explored with exclusive anti-Markovnikov-type regioselectivity, thus affording vicinal fluorohydrins with regioselectivities opposite that of noncatalyzed processes. This reaction is operationally simple, scalable under mild conditions. The mechanism studies and DFT calculations revealed that the reaction go through a radical mechanism.Keywords: anti-Markovnikov; fluorohydrins; radical hydroxyfluorination; silver-catalyzed; styrenes;
Co-reporter:Liyan Wang;Xiaohuan Jiang
Organic Chemistry Frontiers 2017 vol. 4(Issue 10) pp:1958-1961
Publication Date(Web):2017/09/26
DOI:10.1039/C7QO00450H
The first example of a silver-mediated fluorination of alkyl iodides with the Ruppert–Prakash reagent (TMSCF3) as a fluorinating agent has been reported. This reaction is compatible with a variety of functional groups and proceeds under mild reaction conditions. Moreover, we demonstrate that the large surface area of CaF2 dramatically increased the reaction yield.
Co-reporter:Peng Xu;Feng Wang;Guilan Fan; Xiufang Xu; Pingping Tang
Angewandte Chemie International Edition 2017 Volume 56(Issue 4) pp:1101-1104
Publication Date(Web):2017/01/19
DOI:10.1002/anie.201609741
AbstractThe first example of a hypervalent iodine(III)-mediated oxidative fluorination of alkylsilanes by fluoride ions without the use of transition metals is demonstrated. This reaction is operationally simple, scalable, and proceeds under mild reaction conditions. Mechanistic studies suggest the involvement of a single-electron transfer resulting from the interaction of an organopentafluorosilicate and aryliodonium difluoride, which were generated in situ from the corresponding alkylsilane and iodosobenzene, respectively, in the presence of fluoride ions.
Co-reporter:Hengtao Wang;Xiunan Zhang
Chemical Science (2010-Present) 2017 vol. 8(Issue 10) pp:7246-7250
Publication Date(Web):2017/09/25
DOI:10.1039/C7SC03293E
The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished using a nickel-catalyzed cross coupling of alkyl bromide with vinyl stannane as the final step. The other key steps include late-stage C(sp3)–H bromination, the oxidative cleavage of a diol to provide the requisite ketone and ester for schilancidilactones A and B, and Dieckmann-type condensation to generate the A ring of schilancitrilactone A and 20-epi-schilancitrilactone A.
Co-reporter:Rui Guo, Zhengjuan Zhang, Feng Shi, and Pingping Tang
Organic Letters 2016 Volume 18(Issue 5) pp:1008-1011
Publication Date(Web):February 24, 2016
DOI:10.1021/acs.orglett.6b00130
The first example of a mild and tunable cascade reaction of aryl diazonium salts and trialkylamine in the presence of Selectfluor to prepare monofluorinated arylhydrazones and gem-difluorinated azo compounds without metal has been explored. In the presence of H2O, the monofluorinated arylhydrazones were observed in moderate to good yield. In the absence of H2O, the gem-difluorinated azo compounds were obtained. The fluorinated arylhydrazones were utilized to synthesize fluorinated pyrazoles and other nitrogen-containing compounds.
Co-reporter:Rui Guo, Haodong Yang and Pingping Tang
Chemical Communications 2015 vol. 51(Issue 42) pp:8829-8832
Publication Date(Web):17 Apr 2015
DOI:10.1039/C5CC02446C
The first example of silver-catalyzed intermolecular and intramolecular Meerwein fluoroarylation of styrenes with aryl diazonium salts has been developed. This reaction is operationally simple, scalable and proceeds under mild conditions. Furthermore, fluorinated dihydrobenzofurans and indolines were easily accessed using this method.
Co-reporter:Xiaofei Zhang, Haodong Yang, and Pingping Tang
Organic Letters 2015 Volume 17(Issue 23) pp:5828-5831
Publication Date(Web):November 16, 2015
DOI:10.1021/acs.orglett.5b03001
The first example of a practical and selective azidation of unactivated aliphatic C–H bonds with easily handled sulfonyl azides as azide source without the use of transition metals has been explored. This method is operationally simple, scalable, and applicable to late-stage azidation of natural products and derivatives, which make it a valuable method for the synthesis of organic azides.
Co-reporter:Shuo Guo;Xiaofei Zhang ;Dr. Pingping Tang
Angewandte Chemie 2015 Volume 127( Issue 13) pp:4137-4141
Publication Date(Web):
DOI:10.1002/ange.201411807
Abstract
The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives.
Co-reporter:Liang Wang;Hengtao Wang;Yihang Li ;Dr. Pingping Tang
Angewandte Chemie 2015 Volume 127( Issue 19) pp:5824-5827
Publication Date(Web):
DOI:10.1002/ange.201501169
Abstract
The first total syntheses of schilancitrilactones B and C have been accomplished in 17 steps (longest linear sequence) from commercially available materials. Key steps include an intramolecular radical cyclization to provide the seven-membered ring, late-stage iodination, and an intermolecular radical addition reaction to complete the total synthesis.
Co-reporter:Liang Wang;Hengtao Wang;Yihang Li ;Dr. Pingping Tang
Angewandte Chemie International Edition 2015 Volume 54( Issue 19) pp:5732-5735
Publication Date(Web):
DOI:10.1002/anie.201501169
Abstract
The first total syntheses of schilancitrilactones B and C have been accomplished in 17 steps (longest linear sequence) from commercially available materials. Key steps include an intramolecular radical cyclization to provide the seven-membered ring, late-stage iodination, and an intermolecular radical addition reaction to complete the total synthesis.
Co-reporter:Shuo Guo;Xiaofei Zhang ;Dr. Pingping Tang
Angewandte Chemie International Edition 2015 Volume 54( Issue 13) pp:4065-4069
Publication Date(Web):
DOI:10.1002/anie.201411807
Abstract
The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic CH bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives.
Co-reporter:Peng Xu;Shuo Guo;Liyan Wang ;Dr. Pingping Tang
Angewandte Chemie 2014 Volume 126( Issue 23) pp:6065-6068
Publication Date(Web):
DOI:10.1002/ange.201400225
Abstract
A mild and catalytic method to form difluoromethylated arenes through the activation of benzylic CH bonds has been developed. Utilizing AgNO3 as the catalyst, various arenes with diverse functional groups undergo activation/fluorination of benzylic CH bonds with commercially available Selectfluor reagent as a source of fluorine in aqueous solution. The reaction is operationally simple and amenable to gram-scale synthesis.
Co-reporter:Peng Xu;Shuo Guo;Liyan Wang ;Dr. Pingping Tang
Angewandte Chemie International Edition 2014 Volume 53( Issue 23) pp:5955-5958
Publication Date(Web):
DOI:10.1002/anie.201400225
Abstract
A mild and catalytic method to form difluoromethylated arenes through the activation of benzylic CH bonds has been developed. Utilizing AgNO3 as the catalyst, various arenes with diverse functional groups undergo activation/fluorination of benzylic CH bonds with commercially available Selectfluor reagent as a source of fluorine in aqueous solution. The reaction is operationally simple and amenable to gram-scale synthesis.
Co-reporter:Xiaofei Zhang, Shuo Guo and Pingping Tang
Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 7) pp:
Publication Date(Web):
DOI:10.1039/C5QO00095E
Co-reporter:Rui Guo, Haodong Yang and Pingping Tang
Chemical Communications 2015 - vol. 51(Issue 42) pp:NaN8832-8832
Publication Date(Web):2015/04/17
DOI:10.1039/C5CC02446C
The first example of silver-catalyzed intermolecular and intramolecular Meerwein fluoroarylation of styrenes with aryl diazonium salts has been developed. This reaction is operationally simple, scalable and proceeds under mild conditions. Furthermore, fluorinated dihydrobenzofurans and indolines were easily accessed using this method.