Co-reporter:Xinpeng Jiang, Jinkang Chen, Weijie Zhu, Kang Cheng, Yong Liu, Wei-Ke Su, and Chuanming Yu
The Journal of Organic Chemistry October 6, 2017 Volume 82(Issue 19) pp:10665-10665
Publication Date(Web):September 13, 2017
DOI:10.1021/acs.joc.7b01695
Mechanochemical conditions have been applied to a highly efficient cobalt(III)-catalyzed C–H bond activation for the first time. In a subsequent step to the olefin insertion and β-oxygen elimination, N-pyrimidinylindoles were allylated with vinylethylene carbonates in the absence of organic solvent under high-speed ball-milling condition. As the reaction afforded the desired products in up to 98% yields within a short time, this method constitutes an environmentally friendly and powerful alternative to the common solution-based approaches.
Co-reporter:Xinpeng Jiang, Xueyan Wang, Xing Huang, Guizhou Li, Chuanming Yu
Journal of Saudi Chemical Society 2017 Volume 21, Issue 5(Volume 21, Issue 5) pp:
Publication Date(Web):1 July 2017
DOI:10.1016/j.jscs.2017.01.004
The key intermediate of misoprostol, methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate was prepared from commercially available suberic acid in 40% yield over five steps. The key step involved a ZnCl2 catalyzed Friedel-Crafts reaction between furan and 2,9-oxonanedione. Sulfuric acid catalyzed methylation of 8-(furan-2-yl)-8-oxooctanoic acid followed by sequential reduction and ZnCl2 catalyzed Piancatelli rearrangement resulted in the formation of the key intermediate of misoprostol.
Co-reporter:Guanghui Yang;Xinpeng Jiang;Yong Liu;Na Li;Guisen Yin ; Chuanming Yu
Asian Journal of Organic Chemistry 2016 Volume 5( Issue 7) pp:882-885
Publication Date(Web):
DOI:10.1002/ajoc.201600204
Abstract
A novel and efficient palladium-catalyzed cross-coupling benzylation reaction of pentafluorobenzene through selective C−H functionalization has been developed. A series of carbonates and polyfluorobenzenes have been examined and found to give moderate to good yields. This transformation provides a new straightforward approach for the synthesis of fluorinated diarylmethanes.
Co-reporter:Guang-Hui Yang;Ming Liu;Na Li;Ran Wu;Xu Chen;Ling-Ling Pan;Shang Gao;Xing Huang;Chen Wang ;Chuan-Ming Yu
European Journal of Organic Chemistry 2015 Volume 2015( Issue 3) pp:616-624
Publication Date(Web):
DOI:10.1002/ejoc.201403354
Abstract
A highly efficient and simple procedure was developed to synthesize substituted fluorinated nitriles and diaryl ketones under mild conditions from polyfluorobenzenes and phenylacetonitriles. This coupling process was achieved by using a selective C–F bond functionalization without a transition-metal catalyst. The reactions had good functional group tolerance and provided the products in moderate to excellent yields.
Co-reporter:Guanghui Yang, Zhiqun Yu, Xinpeng Jiang, Chuanming Yu
Tetrahedron Letters 2015 Volume 56(Issue 32) pp:4689-4693
Publication Date(Web):5 August 2015
DOI:10.1016/j.tetlet.2015.06.032
A facile and efficient method to synthesize fluorinated aryl ethers with polyfluorobenzenes and carbonates without metal catalyst has been developed. Selective C–F bond and aryl fragment of carbonate participate in the reaction. The desired products were obtained in moderate to excellent yields with good substrates compatibility.
Co-reporter:Ran Wu;Shang Gao;Xu Chen;Guanghui Yang;Lingling Pan;Gaobo Hu;Ping Jia;Weihui Zhong
European Journal of Organic Chemistry 2014 Volume 2014( Issue 16) pp:3379-3386
Publication Date(Web):
DOI:10.1002/ejoc.201402098
Abstract
A facile and efficient one-pot, two-step synthesis of 1,2-disubstituted 3-(1H-tetrazol-5-yl)-2H-isoindoles through Ugi four-component reaction/AgNO3-catalyzed reaction of 2-alkynylbenzaldehydes, amines, isonitriles, and Me3SiN3 is described. This transformation proceeds through 5-exo-dig cyclization, [1,3]-H shift, and [1,5]-H shift to generate the products in moderate to excellent yields.
Co-reporter:Chuanming Yu;Xu Chen;Ran Wu;Guanghui Yang;Jiaoyong Shi ;Lingling Pan
European Journal of Organic Chemistry 2014 Volume 2014( Issue 10) pp:2037-2043
Publication Date(Web):
DOI:10.1002/ejoc.201301612
Abstract
A one-pot two-step synthesis of N-(imidazo[1,2-a]pyridin-3-yl)sulfonamides from easily available arylglyoxal hydrates, 2-aminopyridines, and sulfonamides has been developed. The procedure, using zinc chloride as catalyst, is simple and inexpensive. The desired products were obtained in moderate to good yields under the optimized reaction conditions.
Co-reporter:Jianjun Li, Ping He, Chuanming Yu
Tetrahedron 2012 68(22) pp: 4138-4144
Publication Date(Web):
DOI:10.1016/j.tet.2012.03.104
Co-reporter:Chuanming Yu, Jun Qiu, Fei Zheng, Weihui Zhong
Tetrahedron Letters 2011 Volume 52(Issue 26) pp:3298-3302
Publication Date(Web):29 June 2011
DOI:10.1016/j.tetlet.2011.04.067
A type of secondary–secondary–tertiary triamine bifunctional organocatalysts have been properly designed and synthesized. In our study, the designed catalyst (S)-N-(pyrrolidin-2-ylmethyl)pyridin-2-amine 5 has been shown to be highly efficient to promote the asymmetric Michael addition of ketones to nitroolefins at room temperature, which afforded the corresponding adducts in excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to >99% ee).A type of secondary–secondary–tertiary triamine bifunctional organocatalysts have been properly designed and synthesized. In our study, the designed catalyst (S)-N-(pyrrolidin-2-ylmethyl)pyridin-2-amine 5 has been shown to be highly efficient to promote the asymmetric Michael addition of ketones to nitroolefins at room temperature, which afforded the corresponding adducts in excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to >99% ee).
Co-reporter:Chuan-Ming YU;Bo WANG ;Zhi-Wei CHEN
Chinese Journal of Chemistry 2008 Volume 26( Issue 10) pp:1899-1901
Publication Date(Web):
DOI:10.1002/cjoc.200890341
Abstract
An efficient, economical and easy method for the synthesis of dimethylaminomethylenediphosphonates using bis(trichloromethyl) carbonate and RCONR1R2 has been developed, which proceeded under relatively mild conditions.