Citation:
Lingheng Kong, Fang Xie, Songjie Yu, Zisong Qi, Xingwei Li. Rh(III)-catalyzed coupling of nitrones with alkynes for the synthesis of indolines[J]. Chinese Journal of Catalysis,
;2015, 36(7): 925-932.
doi:
10.1016/S1872-2067(15)60866-X
-
Rh-catalyzed redox-neutral coupling between N-aryl nitrones and alkynes has been achieved under relatively mild conditions. The reaction proceeded via C-H activation at the N-aryl ring with subsequent O-atom transfer, affording trisubstituted indolines in good chemoselectivity and moderate to good diasteroselectivity.
-
-
-
[1]
[1] Chen X, Engle K M, Wang D H, Yu J Q. Angew Chem Int Ed, 2009, 48: 5094
-
[2]
[2] Yeung C S, Dong V M. Chem Rev, 2011, 111: 1215
-
[3]
[3] Wencel-Delord J, Droege T, Liu F, Glorius F. Chem Soc Rev, 2011, 40: 4740
-
[4]
[4] Sun C L, Li B J, Shi Z J. Chem Rev, 2011, 111: 1293
-
[5]
[5] Yamaguchi J, Yamaguchi A D, Itami K. Angew Chem Int Ed, 2012, 51: 8960
-
[6]
[6] McMurray L, O'Hara F, Gaunt M J. Chem Soc Rev, 2011, 40: 1885
-
[7]
[7] Cho S H, Kim J Y, Kwak J, Chang S. Chem Soc Rev, 2011, 40: 5068
-
[8]
[8] Ackermann L. Acc Chem Res, 2014, 47: 281
-
[9]
[9] Ackermann L. Chem Rev, 2011, 111: 1315
-
[10]
[10] Xie F, Qi Z S, Yu S J, Li X W. J Am Chem Soc, 2014, 136: 4780
-
[11]
[11] Kim J Y, Park S H, Ryu J, Cho S H, Kim S H, Chang S. J Am Chem Soc, 2012, 134: 9110
-
[12]
[12] Zhen W C, Du Z Y, Li X W. Chin J Catal (甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34: 679
-
[13]
[13] Zhao D, Nimphius C, Lindale M, Glorius F. Org Lett, 2013, 15: 4504
-
[14]
[14] Qi Z S, Li X W. Chin J Catal (戚自松, 李兴伟. 催化学报), 2015, 36: 48
-
[15]
[15] Zhang F, Spring D R. Chem Soc Rev, 2014, 43: 6906
-
[16]
[16] Kuhl N, Schröder N, Glorius F. Adv Synth Catal, 2014, 356: 1443
-
[17]
[17] Colby D A, Tsai A S, Bergman R G, Ellman J A. Acc Chem Res, 2012, 45: 814
-
[18]
[18] Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41: 3651
-
[19]
[19] Colby D A, Bergman R G, Ellman J A. Chem Rev, 2010, 110: 624
-
[20]
[20] Guimond N, Gouliaras C, Fagnou K. J Am Chem Soc, 2010, 132: 6908
-
[21]
[21] Guimond N, Gorelsky S I, Fagnou K. J Am Chem Soc, 2011, 133: 6449
-
[22]
[22] Patureau F W, Glorius F. Angew Chem Int Ed, 2011, 50: 1977
-
[23]
[23] Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc, 2011, 133: 2350
-
[24]
[24] Huang H W, Ji X C, Wu W Q, Jiang H F. Chem Soc Rev, 2015, 44: 1155
-
[25]
[25] Hyster T K, Rovis T. Chem Commun, 2011, 47: 11846
-
[26]
[26] Martin R M, Bergman R G, Ellman J A. J Org Chem, 2012, 77: 2501
-
[27]
[27] Wang H G, Glorius F. Angew Chem Int Ed, 2012, 51: 7318
-
[28]
[28] Neely J M, Rovis T. J Am Chem Soc, 2013, 135: 66
-
[29]
[29] Huckins J R, Bercot E A, Thiel O R, Hwang T L, Bio M M. J Am Chem Soc, 2013, 135: 14492
-
[30]
[30] Zhang X P, Chen D, Zhao M, Zhao J, Jia A Q, Li X W. Adv Synth Catal, 2011, 353: 719
-
[31]
[31] Huang X L, Huang J S, Du C L, Zhang X Y, Song F J, You J S. Angew Chem Int Ed, 2013, 52: 12970
-
[32]
[32] Cui S L, Zhang Y, Wu Q F. Chem Sci, 2013, 4: 3421
-
[33]
[33] Liu G X, Shen Y Y, Zhou Z, Lu X Y. Angew Chem Int Ed, 2013, 52: 6033
-
[34]
[34] Shen Y Y, Liu G X, Zhou Z, Lu X Y. Org Lett, 2013, 15: 3366
-
[35]
[35] Shi J J, Zhao G G, Wang X W, Xu H E, Yi W. Org Biomol Chem, 2014, 12: 6831
-
[36]
[36] Chen Y, Wang D Q, Duan P P, Ben R, Dai L, Shao X R, Hong M, Zhao J, Huang Y. Nat Commun, 2014, 5: 4610
-
[37]
[37] Chuang S C, Gandeepan P, Cheng C H. Org Lett, 2013, 15: 5750
-
[38]
[38] Liu B Q, Song C, Sun C, Zhou S G, Zhu J. J Am Chem Soc, 2013, 135: 16625
-
[39]
[39] Zhao D B, Shi Z Z, Glorius F. Angew Chem Int Ed, 2013, 52: 12426
-
[40]
[40] Zheng L Y, Hua R M, Chemistry, 2014, 20: 2352
-
[41]
[41] Wang C M, Sun H, Fang Y, Huang Y. Angew Chem Int Ed, 2013, 52: 5795
-
[42]
[42] Matsuda T, Tomaru Y. Tetrahedron Lett, 2014, 55: 3302
-
[43]
[43] Huang X C, Yang X H, Song R J, Li J H. J Org Chem, 2014, 79: 1025
-
[44]
[44] Fan Z L, Song S S, Li W, Geng K J, Xu Y J, Miao Z H, Zhang A. Org Lett, 2015, 17: 310
-
[45]
[45] Zhang Q R, Huang J R, Zhang W, Dong L. Org Lett, 2014, 16: 1684
-
[46]
[46] Yu S J, Liu S, Lan Y, Wan B S, Li X W. J Am Chem Soc, 2015, 137: 1623
-
[47]
[47] Zhang X Y, Qi Z S, Li X W. Angew Chem Int Ed, 2014, 53: 10794
-
[48]
[48] Sharma U, Park Y, Chang S. J Org Chem, 2014, 79: 9899
-
[49]
[49] Qi Z S, Wang M, Li X W. Org Lett, 2013, 15: 5440
-
[50]
[50] Wang C X, Wang D P, Yan H, Wang H L, Pan B, Xin X Y, Li X C, Wu F, Wan B S. Angew Chem Int Ed, 2014, 53: 11940
-
[51]
[51] Ren Z, Mo F Y, Dong G B. J Am Chem Soc, 2012, 134: 16991
-
[52]
[52] Mawo R Y, Mustakim S, Young V G, Hoffmann M R, Smoliakova I P. Organometallics, 2007, 26: 1801
-
[53]
[53] Bielsa R, Navarro R, Urriolabeitia E P, Lledós A. Inorg Chem, 2007, 46: 10133
-
[54]
[54] Williams R M, Cox R J. Acc Chem Res, 2003, 36: 127
-
[55]
[55] Zhang D, Song H, Qin Y. Acc Chem Res, 2011, 44: 447
-
[56]
[56] Takano S, Ogasawara K. Alkaloids, 1989, 36: 225
-
[57]
[57] Mio M J, Kopel L C, Braun J B, Gadzikwa T L, Hull K L, Brisbois R G, Markworth C J, Grieco P A. Org Lett, 2002, 4: 3199
-
[58]
[58] Dateer R B, Chang S. J Am Chem Soc, 2015, 137: 4908
-
[1]
-
-
-
[1]
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
-
[2]
.
CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
. CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -. -
[3]
Jiajia Li , Xiangyu Zhang , Zhihan Yuan , Zhengyang Qian , Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073
-
[4]
Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
-
[5]
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
-
[6]
Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co3O4 as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
-
[7]
Yuan GAO , Yiming LIU , Chunhui WANG , Zhe HAN , Chaoyue FAN , Jie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271
-
[8]
Kaihui Huang , Dejun Chen , Xin Zhang , Rongchen Shen , Peng Zhang , Difa Xu , Xin Li . Constructing Covalent Triazine Frameworks/N-Doped Carbon-Coated Cu2O S-Scheme Heterojunctions for Boosting Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(12): 2407020-. doi: 10.3866/PKU.WHXB202407020
-
[9]
Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
-
[10]
Chengpeng Liu , Yinxia Fu . Design and Practice of Ideological and Political Education for the Public Elective Course “Life Chemistry Experiment” in Universities. University Chemistry, 2024, 39(10): 242-248. doi: 10.12461/PKU.DXHX202404064
-
[11]
Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
-
[12]
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
-
[13]
Jinfu Ma , Hui Lu , Jiandong Wu , Zhongli Zou . Teaching Design of Electrochemical Principles Course Based on “Cognitive Laws”: Kinetics of Electron Transfer Steps. University Chemistry, 2024, 39(3): 174-177. doi: 10.3866/PKU.DXHX202309052
-
[14]
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
-
[15]
Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe2O4@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
-
[16]
Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
-
[17]
Fengmiao Yu , Yang Sheng , Chanyue Li , Bao Li . The Three Lives of Aspirin. University Chemistry, 2024, 39(9): 115-121. doi: 10.12461/PKU.DXHX202402033
-
[18]
Yang WANG , Xiaoqin ZHENG , Yang LIU , Kai ZHANG , Jiahui KOU , Linbing SUN . Mn single-atom catalysts based on confined space: Fabrication and the electrocatalytic oxygen evolution reaction performance. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2175-2185. doi: 10.11862/CJIC.20240165
-
[19]
Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023
-
[20]
Qinjin DAI , Shan FAN , Pengyang FAN , Xiaoying ZHENG , Wei DONG , Mengxue WANG , Yong ZHANG . Performance of oxygen vacancy-rich V-doped MnO2 for high-performance aqueous zinc ion battery. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 453-460. doi: 10.11862/CJIC.20240326
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(235)
- HTML views(14)