Jiang Group

Nanjing University of Science and Technology, School of Chemical Engineering

Publications

Papers

1. Yadong Gao, Chao Yang, Sonlin Bai, Xiaolei Liu, Qingcui Wu, Chao jiang*, Xiangbing Qi*, “Visible-light-induced Nickel-catalyzed Cross-coupling with Alkylzirconocenes from Unactivated Alkenes” Chem, Dec.12, 2019.

DOI:10.1016/j.chempr.2019.12.010

https://www.sciencedirect.com/science/article/abs/pii/S2451929419305571
Significance:First
alkylzirconocenes in light-induced cross-coupling; Chain walking and cross-coupling cascade for remote functionalization of alkenes;Convergent functionalization of alkene mixtures with broad substrate scope; Novel radical coupling mechanism; First AlkyZr radical precursor! Simple visible-light energy source!

说明: http://qigroup.nibs.ac.cn/wp-content/uploads/2019/12/RZr-chemistry-1.jpg

 

2. Shufang Zhao; Wenchao Ma; Mumtaz Yasir; Xinli Zhou; Jintang Cheng; Chao Jiang* “Palladium-Catalyzed C2-Selective Alkynylation of Indoles with BromoalkynesChemistrySelect 2018,3, 13319– 13322.

DOI:10.1002/slct.201803010

https://onlinelibrary.wiley.com/doi/full/10.1002/slct.201803010

Significance:The Pd(II) catalyzed direct C2 alkynylation of indoles bearing N-2-pyrimidyl or N-2-pyridinyl moiety as a site-specific directing group was developed with alkynyl halide. A highly regioselective manner can be achieved on a range of indole substrates with excellent functional group tolerance.

3. Qiumei Wang, Chao Yang, Chao Jiang* “Visible-light-promoted radical acylation/cyclization of alkynoates with aldehydes for the synthesis of 3-acylcoumarins”Org. Biomol. Chem.,2018,16, 8196-8204.

DOI:10.1039/c8ob02232a

https://pubs.rsc.org/en/content/articlelanding/2018/OB/C8OB02232A#!divAbstract

Significance: A new, efficient, and atom-economic visible-light-promoted radical acylation/cyclization of alkynoates with aldehydes was developed for the synthesis of 3-acylcoumarins. The reaction undergoes a domino radical addition/5-exo cyclization, and ester migration to afford the product in moderate to good yields with wide functional group tolerance. The significant feature of this new method is the excellent tolerance of aliphatic aldehydes, which leads to the efficient synthesis of aliphatic 3-acylcoumarins.

 

4. Jingjing Fu; Yadong Gao; Xiangbing Qi; Chao Jiang* “Synthesis of Polysubstituted Pyridines and Indoles by a Palladium-Catalyzed Catellani-type Alkylation-Alkenylation Sequence”ChemistrySelect2018,3, 10164– 10168.

DOI:10.1002/slct.201801890

https://onlinelibrary.wiley.com/doi/full/10.1002/slct.201801890

Significance: The C−H functionalization of heterocycles has attracted extensive attention recently due to the ubiquity of substituted heterocycles in natural products, drugs, and other bioactive molecules. The Catellanitype C−H functionalization, which is a palladiumcatalyzed and norbornenemediated coupling process, can properly overcome the metal poisoning between hetero atoms and metal catalyst.

 

5. Chen Yang, Chong Zhang, Zhansheng Zheng, Chao Jiang, Jun Luo, Yang Du, Bingcheng Hu, Chengguo Sun, Karl O. Christe “Synthesis and Characterization of cyclo-Pentazolate Salts of NH4+, NH3OH+, N2H5+, C(NH2)3+, and N(CH3)4+”J. Am. Chem. Soc.,2018,140, 16488.

DOI:10.1021/jacs.8b05106

https://pubs.acs.org/doi/10.1021/jacs.8b05106

Significance: A breakthrough in polynitrogen chemistry was recently achieved by our bulk synthesis of (N5)6(H3O)3(NH4)4Cl in which the cyclo-pentazolate anions were stabilized extensively by hydrogen bridges with the NH4+ and OH3+ cations.

6. Chao Yang; Jing Wang; Jianhua Li; Wenchao Ma; Kun An; Wei He; Chao Jiang * “Visible‐Light Induced Radical Silylation for the Synthesis of Dibenzosiloles via Dehydrogenative Cyclization”Adv. Synth. Catal.,2018,360, 3049–3054.

DOI:10.1002/adsc.201800417 https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201800417

Significance:A visiblelight induced radical silylation to dibenzosiloles from biarylhydrosilanes is described. The products were obtained in satisfactory yields under mild and water/air compatible conditions, providing an efficient and practical method for the synthesis of difunctionalized siloles by using a cheap organic dye photocatalyst.

 

7. Chao Jiang, Lei Zhang, Chengguo Sun, Chong Zhang, Chen Yang, Jun Chen, Bingcheng Hu* “Response to Comment on “Synthesis and characterization of the pentazolate anion cyclo-N5– in (N5)6(H3O)3(NH4)4Cl”Science,2018,359, aas8953.

DOI:10.1126/science.aas8953

https://science.sciencemag.org/content/359/6381/aas8953

Significance: Huang and Xu argue that the cyclo-N5- ion in (N5)6(H3O)3(NH4)4Cl we described in our report is theoretically unfavorable and is instead protonated. Their conclusion is invalid, as they use an improper method to assess the proton transfer in a solid crystal structure. We present an in-depth experimental and theoretical analysis of (N5)6(H3O)3(NH4)4Cl that supports the results in the original paper.

8. Chengguo Sun, Chong Zhang, Chao Jiang, Chen Yang, Yang Du, Yue Zhao, Bingcheng Hu, Zhansheng Zheng, Karl O Christe* “Synthesis of AgN5 and its extended 3D energetic framework”Nature Commun.,2018,9:1269,

DOI: 10.1038/s41467-018-03678-y.

https://www.nature.com/articles/s41467-018-03678-y?utm_source=other_website&utm_medium=display&utm_content=leaderboard&utm_campaign=JRCN_2_LW_X-moldailyfeed

Significance: we report a solvent-free pentazolate complex, AgN5, and a 3D energetic-framework, [Ag(NH3)2]+[Ag3(N5)4]-, constructed from silver and cyclo-N5-. The complexes are stable up to 90 °C and only Ag and N2 are observed as the final decomposition products. Efforts to isolate pure AgN5 were unsuccessful due to partial photolytical and/or thermal-decomposition to AgN3. Convincing evidence for the formation of AgN5 as the original reaction product is presented. The isolation of a cyclo-N5- complex, devoid of stabilizing molecules and ions, such as H2O, H3O+, and NH4+, constitutes a major advance in pentazole chemistry.

 

9. Daoquan Tu, Jun Luo, Chao Jiang* “Copper-mediated domino C–H iodination and nitration of indoles”Chem. Commun.,2018,54, 2514–2517.

DOI:10.1039/c8cc00267c

https://pubs.rsc.org/en/content/articlelanding/2018/CC/C8CC00267C#!divAbstract

Significance:An efficient and cost-effective copper-mediated aerobic oxidative C–H iodination and nitration of indoles via double C–H functionalization is reported. The domino process proceeds smoothly under mild aerobic conditions to give 3-iodo-2-nitroindoles in one step with high regioselectivity and a broad substrate scope. The mechanism of the iodination step is proposed to proceed via a Cu(III)-iodide species that undergoes electrophilic addition at the C3 position of the indole motif.

10. Wanting Zeng, Moldir Nukeyeva, Qiumei Wang, Chao Jiang *“Synthesis of Unnatural α‑Amino Acid Derivatives via Selective o-C-H Functionalization”Org. Biomol. Chem.,2018,16, 598–608.

DOI:10.1039/c7ob02921g

https://pubs.rsc.org/en/content/articlelanding/2018/OB/C7OB02921G#!divAbstract

Significance:Pd-Catalyzed o-C–H functionalization of α-phenylglycine, 4-hydroxyphenylglycine and phenylalanine using picolinamide as a directing group is reported. We have developed different protocols for the arylation, alkylation, alkynylation, halogenation, alkoxylation, and acyloxylation of these amino acids. The reactions exhibit high selectivity, broad substrate scope, and compatibility with different functional groups in moderate to high yields.

11. Yadong Gao, Wangying Zhu, Long Yin, Bo Dong, Jingjing Fu, Zhiwen Ye, Fengtian Xue, Chao Jiang*“Palladium-catalyzed direct C2-arylation of free (N-H) indoles via norbornene-mediated regioselective C-H activation”Tetrahedron Lett.,2017,58, 2213–2216.

DOI:10.1016/j.tetlet.2017.04.066

https://www.sciencedirect.com/science/article/pii/S0040403917305208?via%3Dihub

Significance:A palladium-catalyzed direct C2-arylation reaction of free (N-H) indoles has been developed. This reaction relies on a norbornene-mediated C-H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.

12. Dongdong Liang, Deanna Sersen, Chao Yang, Jeffrey R. Deschamps, Gregory H. Imler, Chao Jiang, Fengtian Xue.* “One-Pot Sequential Reaction to 2-Substituted-Phenanthridinones from N-Methoxybenzamides”Org. Biomol. Chem.,2017,15, 4390–4398.

DOI:10.1039/c7ob00649g

https://pubs.rsc.org/en/content/articlelanding/2017/OB/C7OB00649G#!divAbstract

Significance The sequential use of a hypervalent iodine reagent leads to the one-pot synthesis of 2-bromo/chloro-phenanthridinones via an amidation of arenes followed by a regioselective halogenation reaction. These consecutive C–H functionalization reactions can be used efficiently to construct 2-substituted-phenanthridinones at room temperature with good to high yields. Application of the current method is highlighted by the concise synthesis of the natural product PJ34.

13.  Zuo, R.; Zhang, Y., Jiang, C.; Hackett, J. C.; Loria, R.; Bruner, S. D.; Ding, Y. S.* “Engineered P450 biocatalysts show improved activity and regiopromiscuity in aromatic nitration” Sci. Rep. 7, 842;

DOI:10.1038/s41598-017-00897-z(2017)

https://dx.doi.org/10.1038/s41598-017-00897-z(2017)

14.  Liang, D.; Yu, W.; Nguyen, N.; Deschamps, J. R.; Imler, G. H.; Li, Y.; MacKerell, A. D.; Jiang, C.; Xue, F. T.* “Iodobenzene-Catalyzed Synthesis ofPhenanthridinones via Oxidative CH AmidationJ. Org. Chem. 2017, 82, 3589–3596.

DOI:10.1021/acs.joc.7b00106

https://pubs.acs.org/doi/10.1021/acs.joc.7b00106

15.  Li, M.; Lv, Z.-W.; Zheng, J.-F.; Hu, J.-H.; Jiang, C.* Ueda, M.; Zhang, X.* and Wang, L.-J.* “Positively Charged Nanofiltration Membrane with Dendritic Surface for Toxic Element Removal” ACS Sustainable Chem. Eng.,2017,5, 784–792.

16.  Cao, W.-W.; Peng, X.-F.; Chen, X.-Q.; Wang, X.; Jin, F.; Li, Q.; Chen, H.-N.; Jiang, C.; Ye, Z.-W.; and Xing, X.-D.* “Facile synthesis of cationic polymer functionalized nanodiamond with high dispersity and antibacterial activity” J Mater Sci., 2017, 52, 1856–1867.

17.  Xu, Y.-G.; Shen, C.; Lin, Q.-H.; Wang, P.-C.;* Jiang, C. and Lu, M.* “1-Nitro-2-trinitromethyl substituted imidazoles: a new family of high performance energetic materials†” J. Mater. Chem. A, 2016, 4, 17791–17800.

DOI:10.1039/c6ta08831g

https://pubs.rsc.org/en/content/articlelanding/2016/TA/C6TA08831G#!divAbstract

18.  Yang, C.; Cheng, G. Y.; Huang, B. F.; Xue, F. T.* and Jiang, C.* “Metal-free regioselective construction of indolin-3-ones via hypervalent iodine oxidation of N-substituted indoles” RSC Adv., 2016, 6, 87134–87141

DOI:10.1039/c6ra19741h

https://pubs.rsc.org/en/content/articlelanding/2016/RA/C6RA19741H#!divAbstract

19.  .Tu, D. Q.; Cheng, X. Z.; Gao, Y. D.; Yang, P. P.; Ding, Y. S.* and Jiang, C.* “Palladium-catalysed direct C-2 methylation of indoles” Org. Biomol. Chem., 2016, 14, 7443–7446.

DOI:10.1039/c6ob01281g

https://pubs.rsc.org/en/content/articlelanding/2016/OB/C6OB01281G#!divAbstract

20.  Le, J.; Gao, Y. D.; Ding, Y. S.* and Jiang, C.* “Cu-mediated C2-dehydrogenative homocoupling of indoles via C–H activation assisted by a removable N-pyrimidyl group” Tetrahedron Lett., 2016, 57, 1728–1731.

21.  Cheng, X. Z.; Chen, Z.; Gao, Y. D.; Xue, F. T.* and Jiang, C.* Aminoquinoline-assisted vinylic C–H arylation of unsubstituted acrylamide for the selective synthesis of Z olefins” Org. Biomol. Chem., 2016, 14, 3298–3306. Highlighted by “SYNFACTS 2016, 12(5), 0487.

DOI:10.1039/c6ob00164e

https://pubs.rsc.org/en/content/articlelanding/2016/OB/C6OB00164E#!divAbstract

22.  Yang, W.; Coutinhoa, A. L.; Jiang, C.* and Xue, F. T.* “Ligand-free copper-mediated N-arylation of spirocyclic lactams” Tetrahedron Lett., 2015, 56, 5599–5603.

DOI:10.1016/j.tetlet.2015.08.051

https://www.sciencedirect.com/science/article/pii/S004040391530006X?via%3Dihub

23.  Zhao, J.; Cheng, X. Z.; Le, J.; Yang, W.; Xue, F. T.; Zhang, X.; Jiang, C.* “Cu-Mediated Direct Regioselective C-2 Chlorination of Indoles” Org. Biomol. Chem., 2015, 13, 9000–9004.

DOI:10.1039/c5ob01228g

https://pubs.rsc.org/en/content/articlelanding/2015/OB/C5OB01228G#!divAbstract

24.  Yang, W.; Sun, X. Y.; Yu, W. B.; Rai, R.; Deschamps, J. R.; Mitchell, L. A.; Jiang, C.; MacKerell, Jr., A. D.; Xue, F. T.* “Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids” Org. Lett. 2015, 17, 3070–3073.

DOI:10.1021/acs.orglett.5b01350

https://pubs.acs.org/doi/10.1021/acs.orglett.5b01350

25.  Carlsen, P. N.; Jiang, C.; Herrick, I. R.; Frontier, A. J.* “Studies toward the AB ring system of the tetrapetalone natural products” Tetrahedron 2015, 71, 5886–5896.

DOI:10.1016/j.tet.2015.05.021

https://www.sciencedirect.com/science/article/pii/S0040402015006651?via%3Dihub