Rhodium(Ⅲ)-catalyzed intermolecular cyclization of anilines with sulfoxonium ylides toward indoles
-
* Corresponding authors.
E-mail addresses: cuixl@hqu.edu.cn (X. Cui), wyj@zzu.edu.cn (Y. Wu)
Citation: Shen Zhihao, Pi Chao, Cui Xiuling, Wu Yangjie. Rhodium(Ⅲ)-catalyzed intermolecular cyclization of anilines with sulfoxonium ylides toward indoles[J]. Chinese Chemical Letters, ;2019, 30(7): 1374-1378. doi: 10.1016/j.cclet.2019.01.033
(a) L. Li, Z. Chen, X. Zhang, Y. Jia, Chem. Rev. 118 (2018) 3752-3832;
(b) L. Meng, Q. Guo, M. Chen, et al., Chin. Chem. Lett. 29 (2018) 1257-1260;
(c) M. Corsello, J. Kim, N. Garg, Chem. Sci. 8 (2017) 5836-5844;
(d) E. Stempel, T. Gaich, Acc. Chem. Res. 49 (2016) 2390-2402;
(e) R.D. Taylor, M. MacCoss, A.D.G. Lawson, J. Med. Chem. 57 (2014) 5845-5859;
(f) D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 103 (2003) 893-930.
(a) J. Manfredi, U.S. Pat. Appl. Publ., 20130261118, 03 Oct. 2013;
(b) I.I. Zaitseva, S.V. Zaitsev, P.O. Berggren, Invest. New. Drug. 34 (2016) 522-529;
(d) L.S. Ross, M.J. Lafuente-Monasterio, T. Sakata-Kato, et al., ACS Infect. Dis. 4 (2018) 508-515;
(f) D. Marie-Thérèse, B. Stéphane, D. Claire, et al., Eur. Pat. Appl. Publ. (2017) WO 2017064216, 20 Apr.
(a) Z. Wang, P. Xie, Y. Xia, Chin. Chem. Lett. 29 (2018) 47-53;
(b) Z. Chen, X. Shi, D. Ge, et al., Chin. Chem. Lett. 28 (2017) 231-234;
(c) B. Zhang, A. Studer, Chem. Soc. Rev. 44 (2015) 3505-3521;
(d) G.R. Humphrey, J.T. Kuethe, Chem. Rev. 106 (2006) 2875-2911.
(a) E. Fischer, F. Jourdan, Ber. Dtsch. Chem. Ges. 16 (1883) 2241-2245;
(b) E. Fischer, O. Hess, Ber. Dtsch. Chem. Ges. 17 (1884) 559-568.
(a) X. Hu, X. Chen, Y. Zhu, et al., Org. Lett. 19 (2017) 3474-3477;
(b) P.V. Reddy, M. Annapurna, P. Srinivas, et al., New J. Chem. 39 (2015) 3399-3404;
(c) J. Chen, L. He, K. Natte, et al., Adv. Synth. Catal. 356 (2014) 2955-2959;
(d) W. Song, L. Ackermann, Chem. Commun. 49 (2013) 6638-6640;
(e) L. Ackermann, A.V. Lygin, Org. Lett. 14 (2012) 764-767;
(f) J. Chen, Q. Pang, Y. Sun, et al., J. Org. Chem. 76 (2011) 3523-3526;
(g) J. Chen, G. Song, C.L. Pan, X. Li, Org. Lett. 12 (2010) 5426-5429;
(h) F. Maassarani, M. Pfeffer, J. Spencer, E. Wehman, J. Organomet. Chem. 466 (1994) 265-271.
(a) K. Yu, Y. Liang, B. Li, et al., Adv. Synth. Catal. 358 (2016) 661-666;
(b) H. Jiang, S. Gao, J. Xu, et al., Adv. Synth. Catal. 358 (2016) 188-194;
(c) G.D. Tang, C.L. Pan, X. Li, Org. Chem. Front. 3 (2015) 87-90;
(d) N. KumaráMishra, S. HoonáHan, I. SuáKim, Chem. Commun. 51 (2015) 17229-17232.
M.K. Manna, G. Bairy, R. Jana, J. Org. Chem. 83 (2018) 8390-8400.
doi: 10.1021/acs.joc.8b01034
L. Jie, L. Wang, D. Xiong, et al., J. Org. Chem. 83 (2018) 10974-10984.
doi: 10.1021/acs.joc.8b01618
(a) C. You, C. Pi, Y. Wu, X. Cui, Adv. Synth. Catal. 360 (2018) 4068-4072;
(b) G. Chen, X. Zhang, R. Jia, et al., Adv. Synth. Catal. 360 (2018) 3781-3787;
(c) P. Hu, Y. Zhang, Y. Xu, et al., Org. Lett. 20 (2018) 2160-2163;
(d) H. Oh, S. Han, A.K. Pandey, et al., J. Org. Chem. 83 (2018) 4070-4077;
(e) X. Wu, H. Xiong, S. Sun, et al., Org. Lett. 20 (2018) 1396-1399;
(f) K.S. Halskov, M.R. Witten, G.L. Hoang, et al., Org. Lett. 20 (2018) 2464-2467;
(g) M. Barday, C. Janot, N.R. Halcovitch, et al., Angew. Chem. Int. Ed. 129 (2017) 13297-13301;
(h) J. Vaitla, A. Bayer, K.H. Hopmann, Angew. Chem. Int. Ed. 56 (2017) 4277-4281.
X. Cui, Z. Ban, W. Tian, et al., Org. Biomol. Chem. 17 (2019) 240-243.
doi: 10.1039/C8OB02818D
(a) Y. Xu, G. Zheng, X. Yang, et al., Chem. Commun. 54 (2018) 670-673;
(b) G. Zheng, M. Tian, Y. Xu, et al., Org. Chem. Front. 5 (2018) 998-1002.
J.S. Sun, M. Liu, J. Zhang, L. Dong, J. Org. Chem. 83 (2018) 10555-10563.
doi: 10.1021/acs.joc.8b01354
T. Yuan, C. Pi, C. You, X. Cui, et al., Chem. Commun. 55 (2019) 163-166.
doi: 10.1039/C8CC08081J
(a) L. Wang, D. Xiong, L. Jie, et al., Chin. Chem. Lett. 29 (2018) 907-910;
(b) F. Xu, Y.J. Li, C. Huang, H.C. Xu, ACS Catal. 8 (2018) 3820-3824.
V.K. Tiwari, N. Kamal, M. Kapur, Org. Lett. 17 (2015) 1766-1769.
doi: 10.1021/acs.orglett.5b00535
T. Okada, K. Nobushige, T. Satoh, M. Miura, Org. Lett. 18 (2016) 1150-1153.
doi: 10.1021/acs.orglett.6b00268
J. Jia, J. Shi, J. Zhou, X. Liu, et al., Chem. Commun. 51 (2015) 2925-2928.
doi: 10.1039/C4CC09823D
(a) L. Xu, T. Li, L. Wang, X. Cui, J. Org. Chem. 84 (2019) 560-567;
(b) Z. Yang, L. Jie, Z. Yao, Z. Yang, X. Cui, Adv. Synth. Catal. 361 (2019) 214-218;
(c) J. Xia, X. Yang, Y. Li, X. Li, Org. Lett. 19 (2017) 3243-3246;
(d) C. Pi, X. Cui, X. Liu, M. Guo, et al., Org. Lett. 16 (2014) 5164-5167;
(e) L. Li, W.W. Brennessel, W.D. Jones, Organometallics 28 (2009) 3492-3500.
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
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
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp3)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
Jindong Hao , Yufen Lv , Shuyue Tian , Chao Ma , Wenxiu Cui , Huilan Yue , Wei Wei , Dong Yi . Additive-free synthesis of β-keto phosphorodithioates via geminal hydro-phosphorodithiolation of sulfoxonium ylides with P4S10 and alcohols. Chinese Chemical Letters, 2024, 35(9): 109513-. doi: 10.1016/j.cclet.2024.109513