Co-reporter:Shuling Yu, Linjun Qi, Kun Hu, Julin Gong, Tianxing Cheng, Qingzong Wang, Jiuxi Chen, and Huayue Wu
The Journal of Organic Chemistry April 7, 2017 Volume 82(Issue 7) pp:3631-3631
Publication Date(Web):March 13, 2017
DOI:10.1021/acs.joc.7b00148
A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.
Co-reporter:Linjun Qi, Kun Hu, Shuling Yu, Jianghe Zhu, Tianxing Cheng, Xiaodong Wang, Jiuxi ChenHuayue Wu
Organic Letters 2017 Volume 19(Issue 1) pp:218-221
Publication Date(Web):December 27, 2016
DOI:10.1021/acs.orglett.6b03499
The first example of the palladium-catalyzed sequential nucleophilic addition followed by an intramolecular cyclization of functionalized nitriles with arylboronic acids has been achieved, providing an efficient synthetic pathway to access structurally diverse isoquinolines and isoquinolones. This methodology has also been successfully applied to the total synthesis of the topoisomerase I inhibitor CWJ-a-5 (free base).
Co-reporter:Shuling Yu;Kun Hu;Julin Gong;Linjun Qi;Jianghe Zhu;Yetong Zhang;Tianxing Cheng
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 20) pp:4300-4307
Publication Date(Web):2017/05/23
DOI:10.1039/C7OB00572E
An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.
Co-reporter:Rui Qiao;Leping Ye;Kun Hu;Shuling Yu;Weiguang Yang;Miaochang Liu;Jinchang Ding;Huayue Wu
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 10) pp:2168-2173
Publication Date(Web):2017/03/08
DOI:10.1039/C6OB02352E
The first example of a copper-catalyzed halogen-free protocol to construct indazolo[3,2-b]quinazolinones was developed through sequential inert C–O bond cleavage followed by intramolecular C–N bond formation. This protocol represents an efficient synthetic tool for accessing a more diverse range of functionalized indazolo[3,2-b]quinazolinones. The structure of the newly synthesized indazolo[3,2-b]quinazolinones was unambiguously confirmed by X-ray crystal diffraction analysis.
Co-reporter:Kun Hu;Linjun Qi;Shuling Yu;Tianxing Cheng;Xiaodong Wang;Zhaojun Li;Yuanzhi Xia;Huayue Wu
Green Chemistry (1999-Present) 2017 vol. 19(Issue 7) pp:1740-1750
Publication Date(Web):2017/04/03
DOI:10.1039/C7GC00267J
A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)–cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.
Co-reporter:Weiguang Yang, Rui Qiao, Jiuxi Chen, Xiaobo Huang, Miaochang Liu, Wenxia Gao, Jinchang Ding, and Huayue Wu
The Journal of Organic Chemistry 2015 Volume 80(Issue 1) pp:482-489
Publication Date(Web):December 1, 2014
DOI:10.1021/jo5024848
A palladium-catalyzed sequential cyclization/C–H activation cascade reaction of 2-amino-N′-arylbenzohydrazides with triethyl orthobenzoates has been developed, providing indazolo[3,2-b]quinazolinones in good to high yields. Two key intermediates of the reaction, 2-phenyl-3-(phenylamino)quinazolinone and C–H insertion palladacycle, were isolated, and their structures were unambiguously confirmed by X-ray crystallography. This method represents an unprecedented example of a halogen-free protocol to access indazolo[3,2-b]quinazolinones. Moreover, this chemistry also provides a useful tool for the discovery of fluorescent materials.
Co-reporter:Yan Shen, Jiuxi Chen, Miaochang Liu, Jinchang Ding, Wenxia Gao, Xiaobo Huang and Huayue Wu
Chemical Communications 2014 vol. 50(Issue 33) pp:4292-4295
Publication Date(Web):09 Jan 2014
DOI:10.1039/C3CC48767A
The first example of the copper-catalyzed direct C–H arylation of pyridine N-oxides with arylboronic esters has been developed, leading to a wide range of 2-arylpyridines in a one-pot synthesis with moderate to good yields without an additional reductant. This transformation allows for rapid access to a variety of 2-arylpyridines using an inexpensive catalytic system that would be more difficult to access with traditional methods. Thus, this method represents a simple and practical procedure to access 2-arylpyridines.
Co-reporter:Weiguang Yang, Jiuxi Chen, Xiaobo Huang, Jinchang Ding, Miaochang Liu, and Huayue Wu
Organic Letters 2014 Volume 16(Issue 20) pp:5418-5421
Publication Date(Web):October 7, 2014
DOI:10.1021/ol5026553
A palladium-catalyzed intramolecular aerobic oxidative C–H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade “rollover” cyclometalation and C–H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.
Co-reporter:Shaoxi Yan, Leping Ye, Miaochang Liu, Jiuxi Chen, Jinchang Ding, Wenxia Gao, Xiaobo Huang and Huayue Wu
RSC Advances 2014 vol. 4(Issue 32) pp:16705-16709
Publication Date(Web):18 Mar 2014
DOI:10.1039/C4RA01605J
A convenient and efficient method for the TFA-catalyzed synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones via a tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids was reported for the first time. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A. Moreover, a plausible mechanism for the formation of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones involving ring-opening and cyclization steps is proposed. The present synthetic route to 3-aryl-2H-benzo[b][1,4]oxazin-2-ones could be readily scaled up to gram quantity without difficulty.
Co-reporter:Fujun Duan, Miaochang Liu, Jiuxi Chen, Jinchang Ding, Yuefei Hu and Huayue Wu
RSC Advances 2013 vol. 3(Issue 46) pp:24001-24004
Publication Date(Web):01 Oct 2013
DOI:10.1039/C3RA41969J
A copper-catalyzed sequential arylation and intramolecular annulation of 2-(2-bromophenyl)-2,3-dihydroquinazolin-4(1H)-ones with alkyl amidines has been developed for the synthesis of 6-alkyl 11bH-quinazolino[3,4-a]quinazolin-13(12H)-ones (3) in moderate to good yields. However, the arylated products N-(2-(4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)phenyl)benzimidamides (4) are isolated when aryl amidines are used in the transformation.
Co-reporter:Tie-Qiang Huang;Wen-Yan Qu;Jin-Chang Ding;Miao-Chang Liu;Hua-Yue Wu;Jiu-Xi Chen
Journal of Heterocyclic Chemistry 2013 Volume 50( Issue 2) pp:293-297
Publication Date(Web):
DOI:10.1002/jhet.1043
A facile and simple catalyst-free protocol has been developed for the condensation of 1,2-diketones with aromatic 1,2-diamines in polyethylene glycol (PEG), providing quinoxaline derivatives in good yields. The important features of the methodology are broad substrates scope, simple workup, catalyst free, environmentally benign, and no requirement for metal catalysts. It is noteworthy that the cyclization reaction of 1,2-diketones with aliphatic 1,2-diamines is also conducted smoothly to afford pyrazines in good yields under the standard conditions. In addition, PEG could be recovered easily and was reused without evident loss in activity
Co-reporter:Xingyong Wang, Miaochang Liu, Long Xu, Qingzong Wang, Jiuxi Chen, Jinchang Ding, and Huayue Wu
The Journal of Organic Chemistry 2013 Volume 78(Issue 11) pp:5273-5281
Publication Date(Web):May 13, 2013
DOI:10.1021/jo400433m
A palladium-catalyzed addition of potassium aryltrifluoroborates to aliphatic nitriles has been developed, leading to a wide range of alkyl aryl ketones with moderate to excellent yields. Moreover, several dinitriles (e.g., malononitrile, glutaronitrile, and adiponitrile) were applicable to this process for the construction of 1,3-, 1,5-, or 1,6-dicarbonyl compounds. The scope of the developed approach is successfully explored toward the one-step synthesis of 2-arylbenzo[b]furans via sequential addition and intramolecular annulation reactions. The methodology accepted a wide range of substrates and is applicable to library synthesis.
Co-reporter:Zhongyan Chen, Jiuxi Chen, Miaochang Liu, Jinchang Ding, Wenxia Gao, Xiaobo Huang, and Huayue Wu
The Journal of Organic Chemistry 2013 Volume 78(Issue 22) pp:11342-11348
Publication Date(Web):October 17, 2013
DOI:10.1021/jo401908g
The first example of a copper-catalyzed cascade reaction of (2-aminophenyl)methanols with aldehydes using the combination of cerium nitrate hexahydrate and ammonium chloride has been developed, leading to a wide range of 2-substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of 2-substituted quinazoline derivatives.
Co-reporter:Miaochang Liu, Shaomiao Lin, Jinchang Ding, Wenxia Gao, Huayue Wu, Jiuxi Chen
Tetrahedron 2013 69(10) pp: 2283-2288
Publication Date(Web):
DOI:10.1016/j.tet.2013.01.024
Co-reporter:Weiguang Yang, Leping Ye, Dayun Huang, Miaochang Liu, Jinchang Ding, Jiuxi Chen, Huayue Wu
Tetrahedron 2013 69(46) pp: 9852-9856
Publication Date(Web):
DOI:10.1016/j.tet.2013.09.012
Co-reporter:Jilei Zhang, Jiuxi Chen, Miaochang Liu, Xingwang Zheng, Jinchang Ding and Huayue Wu
Green Chemistry 2012 vol. 14(Issue 4) pp:912-916
Publication Date(Web):27 Feb 2012
DOI:10.1039/C2GC16539B
The first example of copper-catalyzed coupling of nitroarenes with arylboronic acids was developed, providing diaryl ethers in moderate to excellent yields. The efficiency of this reaction was demonstrated by compatibility with a wide range of groups. Moreover, the rigorous exclusion of air/moisture is not required in these transformations. Thus, the method represents a simple and facile procedure to access diaryl ethers. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from water.
Co-reporter:Jiuxi Chen;Yong Peng;Miaochang Liu;Jinchang Ding;Weike Su;Huayue Wu
Advanced Synthesis & Catalysis 2012 Volume 354( Issue 11-12) pp:2117-2122
Publication Date(Web):
DOI:10.1002/adsc.201100971
Abstract
The first example of a palladium-catalyzed aerobic oxidative coupling of acyl chlorides with arylboronic acids has been developed, leading to a wide range of aryl benzoates in good to excellent yields. This catalytic system shows broad functional group tolerance. Preliminary mechanistic experiments using deuterium labeling showed that the oxygen atom was derived from dioxygen.
Co-reporter:Dayun Huang;Weixing Dan;Jinchang Ding;Miaochang Liu;Huayue Wu
Advanced Synthesis & Catalysis 2012 Volume 354( Issue 11-12) pp:2123-2128
Publication Date(Web):
DOI:10.1002/adsc.201200227
Abstract
An efficient metal-free sulfenylation of indoles with disulfides has been developed, leading to 3-arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2-bromo-3-arylthioindole derivatives in good yield by the one-pot construction of CS and CBr bonds. It is noteworthy that the system enables the use of both the RS moieties in RSSR and shows a broad functional group tolerance.
Co-reporter:Hong-Juan Deng;Yu-Jing Fang;Gao-Wei Chen;Miao-Chang Liu;Hua-Yue Wu ;Jiu-Xi Chen
Applied Organometallic Chemistry 2012 Volume 26( Issue 4) pp:164-167
Publication Date(Web):
DOI:10.1002/aoc.1864
An efficient and convenient copper-catalyzed Clauson–Kass reaction of 2,5-dimethoxytetrahydrofuran with amines in aqueous media has been developed, providing a wide range of N-substituted pyrroles in good yields. It is noteworthy that the Clauson–Kass reaction of 2,5-dimethoxytetrahydrofuran with p-phenylenediamine or m-phenylenediamine proceeds smoothly to afford the corresponding monopyrroles and bispyrroles with high selectivity in impressive yields. A plausible mechanism for the formation of N-substituted pyrroles has been proposed. Copyright © 2012 John Wiley & Sons, Ltd.
Co-reporter:Gaigai Liang;Miaochang Liu;Jinchang Ding;Wenxia Gao;Huayue Wu
Chinese Journal of Chemistry 2012 Volume 30( Issue 7) pp:1611-1616
Publication Date(Web):
DOI:10.1002/cjoc.201200028
Abstract
A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disul?des generating N-(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed.
Co-reporter:Gaigai Liang, Jing Chen, Jiali Chen, Wanmei Li, Jiuxi Chen, Huayue Wu
Tetrahedron Letters 2012 Volume 53(Issue 50) pp:6768-6770
Publication Date(Web):12 December 2012
DOI:10.1016/j.tetlet.2012.09.132
The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.
Co-reporter:Quan-Sheng Ding;Ji-Lei Zhang;Jiu-Xi Chen;Miao-Chang Liu;Jin-Chang Ding;Hua-Yue Wu
Journal of Heterocyclic Chemistry 2012 Volume 49( Issue 2) pp:375-380
Publication Date(Web):
DOI:10.1002/jhet.759
Abstract
Citric acid promoted synthesis of a mini-library 2,3-dihydroquinazolin-4(1H)-ones with good to excellent yields is achieved by tandem reaction of anthranilamides (or anthranilhydrazides) with aldehydes on grinding at room temperature under solvent-free conditions. This method has notable advantages in terms of simple workup, short reaction time, cost-effective, and environmentally benign. J. Heterocyclic Chem., (2012).
Co-reporter:Jiuxi Chen, Xingyong Wang, Xingwang Zheng, Jinchang Ding, Miaochang Liu, Huayue Wu
Tetrahedron 2012 68(43) pp: 8905-8907
Publication Date(Web):
DOI:10.1016/j.tet.2012.08.032
Co-reporter:Xingwang Zheng, Jinchang Ding, Jiuxi Chen, Wenxiao Gao, Miaochang Liu, and Huayue Wu
Organic Letters 2011 Volume 13(Issue 7) pp:1726-1729
Publication Date(Web):March 4, 2011
DOI:10.1021/ol200251x
The coupling of arylboronic acids with electron-deficient nitroarenes was realized for the first time by using a rhodium(I) catalyst under an air atmosphere, achieving unsymmetrical diaryl ethers with yields ranging from poor to good. From a deuterium labeling experiment, the oxygen atom is derived from ambient water. The efficiency of this reaction was demonstrated by its compatibility with fluoro, bromo, chloro, and trifluoromethyl groups.
Co-reporter:Jun Li;Dan-Na Jiang;Jiu-Xi Chen;Miao-Chang Liu;Jin-Chang Ding;Hua-Yue Wu
Journal of Heterocyclic Chemistry 2011 Volume 48( Issue 2) pp:403-406
Publication Date(Web):
DOI:10.1002/jhet.597
Abstract
An efficient and facile synthesis of quinoxaline derivatives in excellent isolated yields by the condensation of 1,2-diamines and 1,2-diketones on grinding under solvent-free conditions at ambient temperature has been developed. The important features of this method are that it is reasonably fast, very clean, high yielding, simple workup, and environmentally benign. J. Heterocyclic Chem., 00, 00 (2011).
Co-reporter:Jilei Zhang, Jiuxi Chen, Jinchang Ding, Miaochang Liu, Huayue Wu
Tetrahedron 2011 67(48) pp: 9347-9351
Publication Date(Web):
DOI:10.1016/j.tet.2011.09.135
Co-reporter:Qiang Zhang;Jiu-Xi Chen;Wen-Xia Gao;Jin-Chang Ding;Hua-Yue Wu
Applied Organometallic Chemistry 2010 Volume 24( Issue 11) pp:809-812
Publication Date(Web):
DOI:10.1002/aoc.1707
Abstract
An efficient and convenient three-component A3 coupling reaction of aldehyde, amine and alkyne via CH activation with CuI alone as the catalyst in PEG is developed, providing a wide range of propargylamines with yields ranging from moderate to excellent. Additionally, the catalyst system was recovered and reused several times without evident loss in activity. Copyright © 2010 John Wiley & Sons, Ltd.
Co-reporter:Wenxue Guo, Guangshu Lv, Jiuxi Chen, Wenxia Gao, Jinchang Ding, Huayue Wu
Tetrahedron 2010 66(13) pp: 2297-2300
Publication Date(Web):
DOI:10.1016/j.tet.2010.02.001
Co-reporter:Xiaoling Xu, Jiuxi Chen, Wenxia Gao, Huayue Wu, Jinchang Ding, Weike Su
Tetrahedron 2010 66(13) pp: 2433-2438
Publication Date(Web):
DOI:10.1016/j.tet.2010.01.086
Co-reporter:Weixing Dan, Hongjuan Deng, Jiuxi Chen, Miaochang Liu, Jinchang Ding, Huayue Wu
Tetrahedron 2010 66(37) pp: 7384-7388
Publication Date(Web):
DOI:10.1016/j.tet.2010.07.023
Co-reporter:Qiang Zhang;Chun-Mei Xu;Jiu-Xi Chen;Xiao-Ling Xu;Jin-Chang Ding;Hua-Yue Wu
Applied Organometallic Chemistry 2009 Volume 23( Issue 12) pp:524-526
Publication Date(Web):
DOI:10.1002/aoc.1559
Abstract
A palladium-catalyzed coupling-type reaction of arylglyoxals with arylboronic acids was achieved by use of trimesitylphosphine as the ligand and K2CO3 as base in toluene, providing symmetrical and unsymmetrical benzil derivatives with yields ranging from moderate to excellent. Of particular mention, the rigorous exclusion of air and moisture is not required in these transformations. Copyright © 2009 John Wiley & Sons, Ltd.
Co-reporter:Wenxue Guo, Jiuxi Chen, Dengze Wu, Jinchang Ding, Fan Chen, Huayue Wu
Tetrahedron 2009 65(27) pp: 5240-5243
Publication Date(Web):
DOI:10.1016/j.tet.2009.04.085
Co-reporter:Shuling Yu, Kun Hu, Julin Gong, Linjun Qi, Jianghe Zhu, Yetong Zhang, Tianxing Cheng and Jiuxi Chen
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 20) pp:NaN4307-4307
Publication Date(Web):2017/03/30
DOI:10.1039/C7OB00572E
An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.
Co-reporter:Rui Qiao, Leping Ye, Kun Hu, Shuling Yu, Weiguang Yang, Miaochang Liu, Jiuxi Chen, Jinchang Ding and Huayue Wu
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 10) pp:NaN2173-2173
Publication Date(Web):2016/12/23
DOI:10.1039/C6OB02352E
The first example of a copper-catalyzed halogen-free protocol to construct indazolo[3,2-b]quinazolinones was developed through sequential inert C–O bond cleavage followed by intramolecular C–N bond formation. This protocol represents an efficient synthetic tool for accessing a more diverse range of functionalized indazolo[3,2-b]quinazolinones. The structure of the newly synthesized indazolo[3,2-b]quinazolinones was unambiguously confirmed by X-ray crystal diffraction analysis.
Co-reporter:Yan Shen, Jiuxi Chen, Miaochang Liu, Jinchang Ding, Wenxia Gao, Xiaobo Huang and Huayue Wu
Chemical Communications 2014 - vol. 50(Issue 33) pp:NaN4295-4295
Publication Date(Web):2014/01/09
DOI:10.1039/C3CC48767A
The first example of the copper-catalyzed direct C–H arylation of pyridine N-oxides with arylboronic esters has been developed, leading to a wide range of 2-arylpyridines in a one-pot synthesis with moderate to good yields without an additional reductant. This transformation allows for rapid access to a variety of 2-arylpyridines using an inexpensive catalytic system that would be more difficult to access with traditional methods. Thus, this method represents a simple and practical procedure to access 2-arylpyridines.