Hydroarylation of terminal alkynes with arylboronic acids catalyzed by low loadings of palladium
-
* Corresponding authors.
E-mail addresses: ndeng@hfut.edu.cn (N. Deng), hjxu@hfut.edu.cn (H. Xu).
Citation: Lei Xu, Shiyu Li, Qi Zhang, Ning Deng, Biao Zhang, Huajian Xu. Hydroarylation of terminal alkynes with arylboronic acids catalyzed by low loadings of palladium[J]. Chinese Chemical Letters, ;2023, 34(2): 107534. doi: 10.1016/j.cclet.2022.05.048
P. Moosophon, S. Kanokmedhakul, K. Kanokmedhakul, K. Soytong, J. Nat. Prod. 72 (2009) 1442–1446.
doi: 10.1021/np800805f
V. Rukachaisirikul, A. Rodglin, Y. Sukpondma, et al., J. Nat. Prod. 75 (2012) 853–858.
doi: 10.1021/np200885e
H.C. Kolb, M.S. VanNieuwenhze, K.B. Sharpless, Chem. Rev. 94 (1994) 2483–2547.
doi: 10.1021/cr00032a009
C. Singh, M. Hassam, V.P. Verma, et al., J. Med. Chem. 55 (2012) 10662–10673.
doi: 10.1021/jm301323k
S.P. Cook, A. Polara, S.J. Danishefsky, J. Am. Chem. Soc. 128 (2006) 16440–16441.
doi: 10.1021/ja0670254
S. Poplata, A. TrÖster, Y.Q. Zou, T. Bach, Chem. Rev. 116 (2016) 9748–9815.
doi: 10.1021/acs.chemrev.5b00723
S.J. Roseblade, A. Pfaltz, Acc. Chem. Res. 40 (2007) 1402–1411.
doi: 10.1021/ar700113g
J. Liu, P. Han, J.X. Liao, et al., J. Org. Chem. 84 (2019) 9344–9352.
doi: 10.1021/acs.joc.9b01056
M.C. Fu, R. Shang, B. Zhao, B. Wang, Y. Fu, Science 363 (2019) 1429–1434.
doi: 10.1126/science.aav3200
T.P. Loh, H.Y. Song, Synlett 12 (2002) 2119–2121.
Z. Liu, J. Derosa, K.M.J. Engle, J. Am. Chem. Soc. 138 (2016) 13076–13081.
doi: 10.1021/jacs.6b08818
B.E. Maryanoff, A.B. Reitz, Chem. Rev. 89 (1989) 863–927.
doi: 10.1021/cr00094a007
D.J. Peterson, J. Org. Chem. 33 (1968) 780–784.
doi: 10.1021/jo01266a061
R.H. Grubbs, S. Chang, Tetrahedron 54 (1998) 4413–4450.
doi: 10.1016/S0040-4020(97)10427-6
A. Fîrstner, Angew. Chem. Int. Ed. 39 (2000) 3012–3043.
doi: 10.1002/1521-3773(20000901)39:17<3012::AID-ANIE3012>3.0.CO;2-G
E. Negishi, Handbook of Organopalladium Chemistry For Organic Synthesis, Wiley-Interscience, New York, 2002.
A.G. Fallis, P. Forgione, Tetrahedron 57 (2001) 5899–5913.
doi: 10.1016/S0040-4020(01)00422-7
K. Fagnou, M. Lautens, Chem. Rev. 103 (2003) 169–196.
doi: 10.1021/cr020007u
A. Biffis, C. Tubaro, M. Baron, Chem. Rev. 16 (2016) 1742–1760.
S. Rao, M.N. Joy, K.R. Prabhu, J. Org. Chem. 83 (2018) 13707–13715.
doi: 10.1021/acs.joc.8b01965
Y. Pang, G. Liu, C. Huang, et al., Angew. Chem. Int. Ed. 59 (2020) 12789–12794.
doi: 10.1002/anie.202004950
N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457–2483.
doi: 10.1021/cr00039a007
T. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara, J. Am. Chem. Soc. 123 (2001) 9918–9919.
doi: 10.1021/ja0165234
E. Shirakawa, G. Takahashi, T. Tsuchimoto, Y. Kawakami, Chem. Commun. (2001) 2688–2689.
C.H. Oh, H.H. Jung, K.S. Kim, N. Kim, Angew. Chem. Int. Ed. 42 (2003) 805–808.
doi: 10.1002/anie.200390214
C.H. Oh, J.H. Ryu, Bull. Korean Chem. Soc. 24 (2003) 1563–1564.
doi: 10.5012/bkcs.2003.24.11.1563
N. Kim, K.S. Kim, A.K. Gupta, C.H. Oh, Chem. Commun. (2004) 618–619.
A.K. Gupta, K.S. Kim, C.H. Oh, Synlett 3 (2005) 457–460.
Y. Yamamoto, N. Kirai, Y. Harada, Chem. Commun. (2008) 2010–2012.
P.S. Lin, M. Jeganmohan, C.H. Cheng, Chem. Eur. J. 14 (2008) 11296–11299.
doi: 10.1002/chem.200801858
X. Xu, J. Chen, W. Gao, et al., Tetrahedron 66 (2010) 2433–2438.
doi: 10.1016/j.tet.2010.01.086
S. Handa, Y. Wang, F. Gallou, B.H. Lipshutz, Science 349 (2015) 1087–1091.
doi: 10.1126/science.aac6936
F.X. Felpin, T. Ayad, S. Mitra, Eur. J. Org. Chem. (2006) 2679–26902006.
J. Magano, J.R. Dunetz, Chem. Rev. 111 (2011) 2177–2250.
doi: 10.1021/cr100346g
S. Handa, M.P. Andersson, F. Gallou, J. Reilly, B.H. Lipshutz, Angew. Chem. Int. Ed. 55 (2016) 4914–4918.
doi: 10.1002/anie.201510570
R.B. Bedford, C.S.J. Cazin, Chem. Commun. (2001) 1540–1541.
N.E. Leadbeater, V.A. Williams, T.M. Barnard, M.J. Collins, Org. Process Res. Dev. 10 (2006) 833–837.
doi: 10.1021/op0600613
Z. Dong, Z. Ye, Adv. Synth. Catal. 356 (2014) 3401–3414.
doi: 10.1002/adsc.201400520
C. Deraedt, L. Salmon, D. Astruc, Adv. Synth. Catal. 356 (2014) 2525–2538.
doi: 10.1002/adsc.201400153
J.Y. Wang, K. Choi, S.J. Zuend, et al., Angew. Chem. Int. Ed. 60 (2021) 399–408.
doi: 10.1002/anie.202011161
A.J. Buckmelter, A.I. Kim, S.D. Rychnovsky, J. Am. Chem. Soc. 122 (2000) 9386–9390.
doi: 10.1021/ja002068k
B. Roschek, K.A. Tallman, C.L. Rector, et al., J. Org. Chem. 71 (2006) 3527–3532.
doi: 10.1021/jo0601462
Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
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
Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
Jian-Rong Li , Jieying Hu , Lai-Hon Chung , Jilong Zhou , Parijat Borah , Zhiqing Lin , Yuan-Hui Zhong , Hua-Qun Zhou , Xianghua Yang , Zhengtao Xu , Jun He . Insight into stable, concentrated radicals from sulfur-functionalized alkyne-rich crystalline frameworks and application in solar-to-vapor conversion. Chinese Journal of Structural Chemistry, 2024, 43(8): 100380-100380. doi: 10.1016/j.cjsc.2024.100380
Haibin Yang , Duowen Ma , Yang Li , Qinghe Zhao , Feng Pan , Shisheng Zheng , Zirui Lou . Mo doped Ru-based cluster to promote alkaline hydrogen evolution with ultra-low Ru loading. Chinese Journal of Structural Chemistry, 2023, 42(11): 100031-100031. doi: 10.1016/j.cjsc.2023.100031
Linjing Li , Wenlai Xu , Jianyong Ning , Yaping Zhong , Chuyue Zhang , Jiane Zuo , Zhicheng Pan . Revealing the intrinsic mechanisms for accelerating nitrogen removal efficiency in the Anammox reactor by adding Fe(II) at low temperature. Chinese Chemical Letters, 2024, 35(8): 109243-. doi: 10.1016/j.cclet.2023.109243
Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
Hualei Xu , Manman Han , Haiqiang Liu , Liang Qin , Lulu Chen , Hao Hu , Ran Wu , Chenyu Yang , Hua Guo , Jinrong Li , Jinxiang Fu , Qichen Hao , Yijun Zhou , Jinchao Feng , Xiaodong Wang . 4-Nitrocatechol as a novel matrix for low-molecular-weight compounds in situ detection and imaging in biological tissues by MALDI-MSI. Chinese Chemical Letters, 2024, 35(6): 109095-. doi: 10.1016/j.cclet.2023.109095
Lijun Yan , Shiqi Chen , Penglu Wang , Xiangyu Liu , Lupeng Han , Tingting Yan , Yuejin Li , Dengsong Zhang . Hydrothermally stable metal oxide-zeolite composite catalysts for low-temperature NOx reduction with improved N2 selectivity. Chinese Chemical Letters, 2024, 35(6): 109132-. doi: 10.1016/j.cclet.2023.109132
Huyi Yu , Renshu Huang , Qian Liu , Xingfa Chen , Tianqi Yu , Haiquan Wang , Xincheng Liang , Shibin Yin . Te-doped Fe3O4 flower enabling low overpotential cycling of Li-CO2 batteries at high current density. Chinese Journal of Structural Chemistry, 2024, 43(3): 100253-100253. doi: 10.1016/j.cjsc.2024.100253
Xinyu Yu , Fei Wu , Xianglang Sun , Linna Zhu , Baoyu Xia , Zhong'an Li . Low-cost dopant-free fluoranthene-based branched hole transporting materials for efficient and stable n-i-p perovskite solar cells. Chinese Chemical Letters, 2024, 35(10): 109821-. doi: 10.1016/j.cclet.2024.109821