Transition-metal-free coupling reactions involving gem–diborylalkanes
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* Corresponding author.
E-mail address: liuzhenxing@zzu.edu.cn (Z. Liu).
Citation: Yongli Li, Dalong Shen, Hao Zhang, Zhenxing Liu. Transition-metal-free coupling reactions involving gem–diborylalkanes[J]. Chinese Chemical Letters, ;2023, 34(7): 108048. doi: 10.1016/j.cclet.2022.108048
K.C. N.icolaou, P.G. B.ulger, D. Sarlah, Angew. Chem. Int. Ed. 44 (2005) 4442–4489.
doi: 10.1002/anie.200500368
J. Magano, J.R. D.unetz, Chem. Rev. 111 (2011) 2177–2250.
doi: 10.1021/cr100346g
C.C.C. Johansson Seechurn, M.O. K.itching, T.J. C.olacot, V. Snieckus, Angew. Chem. Int. Ed. 51 (2012) 5062–5085.
doi: 10.1002/anie.201107017
C.E. G.arrett, K. Prasad, Adv. Synth. Catal. 346 (2004) 889–900.
doi: 10.1002/adsc.200404071
C.L. Sun, Z.J. Shi, Chem. Rev. 114 (2014) 9219–9280.
doi: 10.1021/cr400274j
W. Jo, J.H. L.ee, S.H. C.ho, Chem. Commun. 57 (2021) 4346–4353.
doi: 10.1039/d1cc01048d
Y. Hu, W. Sun, C. Liu, Synlett 30 (2019) 1105–1110.
doi: 10.1055/s-0037-1611728
C. Wu, J. Wang, Tetrahedron Lett. 59 (2018) 2128–2140.
doi: 10.1016/j.tetlet.2018.04.061
R. Nallagonda, K. Padala, A. Masarwa, Org. Biomol. Chem. 16 (2018) 1050–1064.
doi: 10.1039/c7ob02978k
N, Miralles, R.J. M.aza, E. Fernández, Adv. Synth. Catal. 360 (2018) 1306–1327.
doi: 10.1002/adsc.201701390
S. Li, J. Li, T. Xia, W. Zhao, Chin. J. Chem. 37 (2019) 462–468.
doi: 10.1002/cjoc.201800575
D.S. M.atteson, R.J. M.ood, P.K. J.esthi, J. Am. Chem. Soc. 97 (1975) 5608–5609.
doi: 10.1021/ja00852a062
D.S. M.atteson, R.J. M.oody, J. Am. Chem. Soc. 99 (1977) 3196–3197.
doi: 10.1021/ja00451a071
D.S. M.atteson, R.J. M.oody, Organometallics 1 (1982) 20–28.
doi: 10.1021/om00061a005
T. Mukaiyama, M. Murakami, T. Oriyama, M. Yamaguchi, Chem. Lett. 10 (1981) 1193–1196.
doi: 10.1246/cl.1981.1193
(a) C. Zhang, W. Hu, J.P. M.orken, ACS Catal. 11 (2021) 10660–10680.
S. Paul, K.K. D.as, D. Aich, S. Manna, S. Panda, Org. Chem. Front. 9 (2022) 838–852.
doi: 10.1039/d1qo01300a
E. Fernández, R. Gava, Org. Biomol. Chem. 17 (2019) 6317–6325.
doi: 10.1039/C9OB00989B
F. Zhang, S. Liao, L. Zhou, et al., Chin. J. Chem. 40 (2022) 582–588.
doi: 10.1002/cjoc.202100701
K. Hong, X. Liu, J.P. M.orken, J. Am. Chem. Soc. 136 (2014) 10581–10584.
doi: 10.1021/ja505455z
Y. Lee, S.-y Baek, J. Park, et al., J. Am. Chem. Soc. 139 (2017) 976–984.
doi: 10.1021/jacs.6b11757
W. Jo, J. Kim, S. Choi, S.H. C.ho, Angew. Chem. Int. Ed. 55 (2016) 9690–9694.
doi: 10.1002/anie.201603329
W. Jo, S. Baek, C. Hwang, et al., J. Am. Chem. Soc. 142 (2020) 13235–13245.
doi: 10.1021/jacs.0c06827
K. Endo, M. Hirokami, T. Shibata, J. Org. Chem. 75 (2010) 3469–3472.
doi: 10.1021/jo1003407
K. Endo, A. Sakamoto, T. Ohkubo, T. Shibata, Chem. Lett. 40 (2011) 1440–1442.
doi: 10.1246/cl.2011.1440
E.L. C.ascia, A.B. C.uenca, E. Fernández, Chem. Eur. J. 22 (2016) 18737–18741.
doi: 10.1002/chem.201604782
J.R. C.oombs, L. Zhang, J.P. M.orken, Org. Lett. 17 (2015) 1708–1711.
doi: 10.1021/acs.orglett.5b00480
S. Namirembe, C. Gao, R.P. W.exler, J.P. M.orken, Org. Lett. 21 (2019) 4392–4394.
doi: 10.1021/acs.orglett.9b01663
C.E. I.acono, T.C. S.tephens, T.S. R.ajan, G. Pattison, J. Am. Chem. Soc. 140 (2018) 2036–2040.
doi: 10.1021/jacs.7b12941
B. Lee, P.J. C.hirik, J. Am. Chem. Soc. 142 (2020) 2429–2437.
doi: 10.1021/jacs.9b11944
W. Sun, L. Wang, C. Xia, C. Liu, Angew. Chem. Int. Ed. 57 (2018) 5501–5505.
doi: 10.1002/anie.201801679
L.H. Zou, M. Fan, L. Wang, C. Liu, Chin. Chem. Lett. 31 (2020) 1911–1913.
doi: 10.1016/j.cclet.2019.12.016
W. Sun, L. Wang, Y. Hu, et al., Nat Commun. 11 (2020) 3113–3123.
doi: 10.1038/s41467-020-16948-5
C. Wu, Z. Bao, B. Dou, J. Wang, Chem. Eur. J. 27 (2021) 2294–2298.
doi: 10.1002/chem.202004581
Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
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
Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe2O4@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO3−x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
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
Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO2F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
Shu Lin , Kezhen Qi . Phase-dependent lithium-alloying reactions for lithium-metal batteries. Chinese Chemical Letters, 2024, 35(4): 109431-. doi: 10.1016/j.cclet.2023.109431
Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
Jiayuan Liang , Xin Mi , Songhao Guo , Hui Luo , Kejun Bu , Tonghuan Fu , Menglin Duan , Yang Wang , Qingyang Hu , Rengen Xiong , Peng Qin , Fuqiang Huang , Xujie Lü . Pressure-induced emission in 0D metal halide (EATMP)SbBr5 by regulating exciton-phonon coupling. Chinese Journal of Structural Chemistry, 2024, 43(7): 100333-100333. doi: 10.1016/j.cjsc.2024.100333
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Tian Yang , Yi Liu , Lina Hua , Yaoyao Chen , Wuqian Guo , Haojie Xu , Xi Zeng , Changhao Gao , Wenjing Li , Junhua Luo , Zhihua Sun . Lead-free hybrid two-dimensional double perovskite with switchable dielectric phase transition. Chinese Chemical Letters, 2024, 35(6): 108707-. doi: 10.1016/j.cclet.2023.108707
Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
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