Stereoselective in situ assembled hydrofunctionalization and cascade
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* Corresponding author.
E-mail address: hezt@sioc.ac.cn (Z.-T. He).
1 These authors contributed equally to this work.
Citation:
Li-Hong Xiong, Liang Chen, Zhi-Tao He. Stereoselective in situ assembled hydrofunctionalization and cascade[J]. Chinese Chemical Letters,
;2026, 37(3): 111921.
doi:
10.1016/j.cclet.2025.111921
P. Koschker, B. Brei, Acc. Chem. Res. 49 (2016) 1524–1536.
doi: 10.1021/acs.accounts.6b00252
Y. Zheng, W. Zi, Tetrahedron Lett. 59 (2018) 2205–2213.
doi: 10.1016/j.tetlet.2018.04.057
G. Li, X. Huo, X. Jiang, et al., Chem. Soc. Rev. 49 (2020) 2060–2118.
doi: 10.1039/c9cs00400a
N.J. Adamson, S.J. Malcolmson, ACS Catal. 10 (2020) 1060–1076.
doi: 10.1021/acscatal.9b04712
R. Blieck, M. Taillefer, F. Monnier, Chem. Rev. 120 (2020) 13545–13598.
doi: 10.1021/acs.chemrev.0c00803
A. Flaget, C. Zhang, C. Mazet, ACS Catal. 12 (2022) 15638–15647.
doi: 10.1021/acscatal.2c05251
G. Cera, G. Maestri, ChemCatChem 14 (2022) e202200295.
doi: 10.1002/cctc.202200295
C. Ma, Y.W. Chen, Z.T. He, Sci. Sin. Chim. 53 (2023) 474–484.
doi: 10.1360/ssc-2022-0196
Y.C. Wang, J.B. Liu, Z.T. He, Chin. J. Org. Chem. 43 (2023) 2614–2627.
doi: 10.6023/cjoc202302010
F. Panahi, F. Bauer, B. Breit, Acc. Chem. Res. 56 (2023) 3676–3693.
doi: 10.1021/acs.accounts.3c00322
L. Li, S. Wang, A. Jakhar, et al., Green Synth. Catal. 4 (2023) 124–134.
doi: 10.1117/12.2660370
J.M. Zhang, Z.T. He, Chin. J. Org. Chem. 45 (2025) 592–601.
doi: 10.6023/cjoc202406047
K. Takahashi, A. Miyake, G. Hata, Bull. Chem. Soc. Jpn. 45 (1972) 1183–1191.
doi: 10.1246/bcsj.45.1183
R.W. Armbruster, M.M. Morgan, J.L. Schmidt, et al., Organometallics 5 (1986) 234–237.
doi: 10.1021/om00133a011
P.W. Jolly, N. Kokel, Synthesis 1990 (1990) 771–773.
doi: 10.1055/s-1990-27010
B.M. Trost, L. Zhi, Tetrahedron Lett. 33 (1992) 1831–1834.
doi: 10.1016/S0040-4039(00)74154-2
O. Löber, M. Kawatsura, J.F. Hartwig, J. Am. Chem. Soc. 123 (2001) 4366–4367.
doi: 10.1021/ja005881o
B.M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 125 (2003) 4438–4439.
doi: 10.1021/ja029190z
L.M. Lutete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 126 (2004) 1622–1623.
doi: 10.1021/ja039774g
B.M. Trost, J. Xie, J.D. Sieber, J. Am. Chem. Soc. 133 (2011) 20611–20622.
doi: 10.1021/ja209244m
N.J. Adamson, E. Hull, S.J. Malcolmson, J. Am. Chem. Soc. 139 (2017) 7180–7183.
doi: 10.1021/jacs.7b03480
N.J. Adamson, K.C.E. Wilbur, S.J. Malcolmson, J. Am. Chem. Soc. 140 (2018) 2761–2764.
doi: 10.1021/jacs.7b13300
S.Z. Nie, R.T. Davison, V.M. Dong, J. Am. Chem. Soc. 140 (2018) 16450–16454.
doi: 10.1021/jacs.8b11150
Q. Zhang, H. Yu, L. Shen, et al., J. Am. Chem. Soc. 141 (2019) 14554–14559.
doi: 10.1021/jacs.9b07600
Z. Zhang, F. Xiao, H.M. Wu, et al., Org. Lett. 22 (2020) 569–574.
doi: 10.1021/acs.orglett.9b04341
C.I. Onyeagusi, X. Shao, S.J. Malcolmson, Org. Lett. 22 (2020) 1681–1685.
doi: 10.1021/acs.orglett.0c00342
H. Yang, D. Xing, Chem. Commun. 56 (2020) 3721–3724.
doi: 10.1039/d0cc00265h
Q. Zhang, D. Dong, W.W. Zi, J. Am. Chem. Soc. 142 (2020) 15860–15869.
doi: 10.1021/jacs.0c05976
M.M. Li, L. Cheng, L.J. Xiao, et al., Angew. Chem. Int. Ed. 60 (2021) 2948–2951.
doi: 10.1002/anie.202012485
A.Y. Jiu, H.S. Slocumb, C.S. Yeung, et al., Angew. Chem. Int. Ed. 60 (2021) 19660–19664.
doi: 10.1002/anie.202105679
Q. Zhang, M. Zhu, W.W. Zi, Chem 8 (2022) 2784–2796.
doi: 10.1016/j.chempr.2022.07.014
Y.C. Wang, Z.X. Xiao, M. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202215568.
doi: 10.1002/anie.202215568
S.Q. Yang, A.J. Han, Y. Liu, et al., J. Am. Chem. Soc. 145 (2023) 3915–3925.
doi: 10.1021/jacs.2c11843
J.M. Zhang, Y.C. Wang, L. Chen, et al., Chem. Eur. J. 30 (2024) e202401350.
doi: 10.1002/chem.202401350
L.M. Lutete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 126 (2004) 1622–1623.
doi: 10.1021/ja039774g
J.T.D. Lee, Y. Zhao, Chem. Eur. J. 24 (2018) 9520–9524.
doi: 10.1002/chem.201802273
M.S. Wu, Z.Y. Han, L.Z. Gong, Org. Lett. 23 (2021) 636–641.
doi: 10.1021/acs.orglett.0c03466
J. Zhang, Y.N. Wang, C. You, et al., Org. Lett. 24 (2022) 1186–1189.
doi: 10.1021/acs.orglett.1c04334
M.Q. Tang, Z.J. Yang, Z.T. He, Nat. Commun. 14 (2023) 6303.
doi: 10.1038/s41467-023-42160-2
Y. Lin, W. Wen, J.H. Liu, et al., Org. Lett. 26 (2024) 7908–7913.
doi: 10.1021/acs.orglett.4c02840
Y. Liu, H. Chen, X. Wang, J. Am. Chem. Soc. 146 (2024) 28427–28436.
doi: 10.1021/jacs.4c09983
Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 116 (1994) 6019–6020.
doi: 10.1021/ja00092a083
B.M. Trost, V.J. Gerusz, J. Am. Chem. Soc. 117 (1995) 5156–5157.
doi: 10.1021/ja00123a020
Y. Yamamoto, M. Al-Masum, Synlett 1995 (1995) 969–970.
doi: 10.1055/s-1995-5148
M. Li, S. Datta, D.M. Barber, et al., Org. Lett. 14 (2012) 6350–6353.
doi: 10.1021/ol303128s
H. Zhou, Y. Wang, L. Zhang, et al., J. Am. Chem. Soc. 139 (2017) 3631–3634.
doi: 10.1021/jacs.7b00437
Z. Wu, M. Zhang, Y. Shi, et al., Org. Chem. Front. 7 (2020) 1502–1511.
doi: 10.1039/d0qo00174k
M. Zhu, Q. Zhang, W.W. Zi, Angew. Chem. Int. Ed. 60 (2021) 6545–6552.
doi: 10.1002/anie.202014510
H.C. Lin, G.J. Knox, C.M. Pearson, et al., Angew. Chem. Int. Ed. 61 (2022) e202201753.
doi: 10.1002/anie.202201753
M. Zhu, P. Wang, Q. Zhang, et al., Angew. Chem. Int. Ed. 61 (2022) e202207621.
doi: 10.1002/anie.202207621
J.H. Liu, Q. Zhou, Y. Lin, et al., ACS Catal. 13 (2023) 6013–6022.
doi: 10.1021/acscatal.3c00790
M.Q. Tang, Z.J. Yang, A.J. Han, et al., Angew. Chem. Int. Ed. 64 (2025) e202413428.
doi: 10.1002/anie.202413428
M.M. Salter, V. Gevorgyan, S. Saito, et al., Chem. Commun. 32 (1996) 17–18.
V. Gevorgyan, C. Kadowaki, M.M. Salter, et al., Tetrahedron 53 (1997) 9097–9106.
doi: 10.1016/S0040-4020(97)00602-9
U. Radhakrishnan, M. Al-Masum, Y. Yamamoto, Tetrahedron Lett. 39 (1998) 1037–1040.
doi: 10.1016/S0040-4039(97)10697-9
N.J. Adamson, H. Jeddi, S.J. Malcolmson, J. Am. Chem. Soc. 141 (2019) 8574–8583.
doi: 10.1021/jacs.9b02637
H. Tsukamoto, T. Konno, K. Ito, et al., Org. Lett. 21 (2019) 6811–6814.
doi: 10.1021/acs.orglett.9b02439
S.Q. Yang, Y.F. Wang, W.C. Zhao, et al., J. Am. Chem. Soc. 143 (2021) 7285–7291.
doi: 10.1021/jacs.1c03157
L. Li, S. Wang, P. Luo, et al., Nat. Commun. 12 (2021) 5667.
doi: 10.1038/s41467-021-25981-x
Q. Li, X. Fang, R. Pan, et al., J. Am. Chem. Soc. 144 (2022) 11364–11376.
doi: 10.1021/jacs.2c03620
C. You, M. Shi, X. Mi, et al., Nat. Commun. 14 (2023) 2911.
doi: 10.1038/s41467-023-38488-4
M. Eaton, Y. Dai, Z. Wang, et al., J. Am. Chem. Soc. 145 (2023) 21638–21645.
doi: 10.1021/jacs.3c08151
B.Y. Xie, Z.T. He, ACS Catal. 14 (2024) 9742–9751.
doi: 10.1021/acscatal.4c02377
R.C. Larock, Y.D. Lu, A.C. Bain, et al., J. Org. Chem. 56 (1991) 4589–4590.
doi: 10.1021/jo00015a002
R.C. Larock, Y. Wang, Y. Lu, et al., J. Org. Chem. 59 (1994) 8107–8114.
doi: 10.1021/jo00105a030
Y. Wang, X. Dong, R.C. Larock, J. Org. Chem. 68 (2003) 3090–3098.
doi: 10.1021/jo026716p
H. Pang, D. Wu, H. Cong, et al., ACS Catal. 9 (2019) 8555–8560.
doi: 10.1021/acscatal.9b02747
Y. Zhang, H.C. Shen, Y.Y. Li, et al., Chem. Commun. 55 (2019) 3769–3772.
doi: 10.1039/c9cc01379b
D. Zhu, Z. Jiao, Y.R. Chi, et al., Angew. Chem. Int. Ed. 59 (2020) 5341–5345.
doi: 10.1002/anie.201915864
Y.W. Chen, Y. Liu, H.Y. Lu, et al., Nat. Commun. 12 (2021) 5626.
doi: 10.1038/s41467-021-25978-6
Q.Y. Liao, C. Ma, Y.C. Wang, et al., Chin. Chem. Lett. 34 (2023) 108371.
doi: 10.1016/j.cclet.2023.108371
H.Z. Miao, Y. Liu, Y.W. Chen, et al., Synlett 34 (2023) 451–456.
doi: 10.1055/a-1916-2937
X. Wang, H.Z. Miao, G.Q. Lin, Z.T. He, Angew. Chem. Int. Ed. 62 (2023) e202301556.
doi: 10.1002/anie.202301556
X.X. Chen, H. Luo, Y.W. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202307628.
doi: 10.1002/anie.202307628
Y.L. Su, L.L. Li, X.L. Zhou, et al., Org. Lett. 20 (2018) 2403–2406.
doi: 10.1021/acs.orglett.8b00740
X. Fang, Q. Li, R. Shi, et al., Org. Lett. 20 (2018) 6084–6088.
doi: 10.1021/acs.orglett.8b02481
L. Liao, R. Jana, K.B. Urkalan, et al., J. Am. Chem. Soc. 133 (2011) 5784–5787.
doi: 10.1021/ja201358b
V. Saini, M.S. Sigman, J. Am. Chem. Soc. 134 (2012) 11372–11375.
doi: 10.1021/ja304344h
M.S. McCammant, T. Shigeta, M.S. Sigman, Org. Lett. 18 (2016) 1792–1795.
doi: 10.1021/acs.orglett.6b00517
D. Wu, H. Pang, G. Yin, Chin. Chem. Lett. 34 (2023) 108087.
doi: 10.1016/j.cclet.2022.108087
R.X. Liang, Y.X. Jia, Acc. Chem. Res. 55 (2022) 734–745.
doi: 10.1021/acs.accounts.1c00781
X.S. Zhang, Y.P. Han, Y. Zhang, et al., Adv. Synth. Catal. 365 (2023) 2436–2466.
doi: 10.1002/adsc.202300476
A.V. Narsaiah, P. Narsimha, Med. Chem. Res. 21 (2012) 538–541.
doi: 10.1007/s00044-011-9556-x
Tingting Zhang , Jing Zhang . Photocatalyzed hydrogen transfer enabled three-component radical cascade reactions: Direct access to thioesters from primary alcohols, elemental sulfur and alkenes. Chinese Chemical Letters, 2026, 37(1): 111131-. doi: 10.1016/j.cclet.2025.111131
Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
Ze-Hong Zheng , Mu-Qiu Chen , Jin Zhou , Jie Wang , Yan-Rong Wei , Cheng Peng , Gu Zhan , Qian-Qian Yang , Bo Han . Diverse synthesis of bridged bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.02,7]oct-3-ene frameworks via stepwise cascade reactions. Chinese Chemical Letters, 2025, 36(12): 111202-. doi: 10.1016/j.cclet.2025.111202
Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
Xiao-Gang Wang , Ai-E Wang , Pei-Qiang Huang . Corrigendum to "A concise formal stereoselective total synthesis of (–)-swainsonine" [Chin Chem Lett 25 (2014) 193–196]. Chinese Chemical Letters, 2025, 36(3): 110597-. doi: 10.1016/j.cclet.2024.110597
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