Citation: Jinhuan Dong, Mengying Jia, Xianxiu Xu. Aryl groups, supplement of amino protecting group chemistry![J]. Chinese Chemical Letters, ;2021, 32(6): 1831-1833. doi: 10.1016/j.cclet.2021.01.034 shu

Aryl groups, supplement of amino protecting group chemistry!

College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science, Shandong Normal University, Ji'nan 250014, China

xuxx677@sdnu.edu.cn

Received Date: 2 December 2020
Revised Date: 4 January 2021
Accepted Date: 12 January 2021
Available Online: 27 January 2021

Figures(1)

Amino group protective strategy has consequently emerged in multistep organic synthesis. Easy and selective deprotection procedures are crucial to facilitate the chemical transformation. Recently, Zhang's group from Henan Normal University collaborating with Chen's group of Nankai University developed a novel strategy for the regiospecific cleavage of inert aryl C—N bonds in N-aryl amides by hypervalent iodine(V) reagents. These procedures allow removal of sort of aryl groups under mild conditions to give primary amides in high efficiency. It bestows these aryl groups with the characteristics of amino protecting groups that might be the supplement of amino protecting group chemistry.
- Organoiodine(V) reagent,
- C(aryl)—N bond cleavage,
- Amino protecting group,
- Dearylation,
- 8-Aminoquinoline,
- Primary amide
1. [1]
  (a) X.L. Han, P.P. Lin, Q. Li, Chin. Chem. Lett. 30 (2019) 1495-1502;
  (b) H. Xia, Y. An, X. Zeng, J. Wu, Chem. Commun. 53 (2017) 12548-12551;
  (c) Z.Z. Zhang, Y.Q. Han, B.B. Zhan, S. Wang, B.F. Shi, Angew. Chem. Int. Ed. 56 (2017) 13145-13149;
  (d) X. Lu, B. Xiao, R. Shang, L. Liu, Chin. Chem. Lett. 27 (2016) 305-311.
2. [2]
  (a) H. Wang, Z. Bai, T. Jiao, et al., J. Am. Chem. Soc. 140 (2018) 3542-3546;
  (b) T. Deguchi, H.L. Xin, H. Morimoto, T. Ohshima, ACS Catal. 7 (2017) 3157-3161;
  (c) M. Berger, R. Chauhan, C.A.B. Rodrigues, N. Maulide, Chem. Eur. J. 22 (2016) 16805-16808;
  (d) T. Ly Dieu, O. Daugulis, Angew. Chem. Int. Ed. 51 (2012) 5188-5191;
  (e) D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 132 (2010) 3965-3972;
  (f) Y. Feng, G. Chen, Angew. Chem. Int. Ed. 49 (2010) 958-961;
  (g) G. He, S.Y. Zhang, W.A. Nack, Q. Li, G. Chen, Angew. Chem. Int. Ed. 52 (2013) 11124-11128;
  (h) D.R. Kronenthal, C.Y. Han, M.K. Taylor, J. Org. Chem. 47 (1982) 2765-2768.
3. [3]
  S.E. Wang, L. Wang, Q. He, R. Fan, Angew. Chem. Int. Ed. 54 (2015) 13655-13658. doi: 10.1002/anie.201508161
4. [4]
  (a) P. Guo, J.H. Huang, Q.C. Huang, X.H. Qian, Chin. Chem. Lett. 24 (2013) 957-961;
  (b) A.T. Hewson, D.A. Sharpe, A.H. Wadsworth, Synth. Commun. 19 (1989) 2095-2099.
5. [5]
  (a) T. Taniguchi, M. Imoto, M. Takeda, et al., Tetrahedron 72 (2016) 4132-4140;
  (b) T. Koreeda, T. Kochi, F. Kakiuchi, Organometallics 32 (2013) 682-690;
  (c) T. Koreeda, T. Kochi, F. Kakiuchi, J. Am. Chem. Soc. 131 (2009) 7238-7239;
  (d) S. Ueno, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 129 (2007) 6098-6099;
  (e) U. Azzena, M. Cattari, G. Melloni, L. Pisano, Synthesis 2003 (2003) 2811-2814.
6. [6]
  L.I. Robins, E.J. Fogle, J.F. Marlier, BBA-Proteins Proteom. 1854 (2015) 1756-1767. doi: 10.1016/j.bbapap.2014.12.016
7. [7]
  S.J. Blanksby, G.B. Ellison, Acc. Chem. Res. 36 (2003) 255-263. doi: 10.1021/ar020230d
8. [8]
  M. Tobisu, K. Nakamura, N. Chatani, J. Am. Chem. Soc. 136 (2014) 5587-5590. doi: 10.1021/ja501649a
9. [9]
  K.J. Geng, Z.L. Fan, A. Zhang, Org. Chem. Front. 3 (2016) 349-353. doi: 10.1039/C5QO00387C
10. [10]
  (a) M. Song, Z. Zhang, D. Zheng, et al., Chin. J. Org. Chem. 40 (2020) 2433-2441;
  (b) Z. Zhang, X. Li, M. Song, et al., J. Org. Chem. 84 (2019) 12792-12799;
  (c) Z. Zhang, D. Zheng, Y. Wan, et al., J. Org. Chem. 83 (2018) 1369-1376.
11. [11]
  K.C. Nicolaou, K. Sugita, P.S. Baran, Y.L. Zhong, J. Am. Chem. Soc. 124 (2002) 2221-2232. doi: 10.1021/ja012125p
12. [12]
  K.C. Nicolaou, P.S. Baran, Y.L. Zhong, K. Sugita, J. Am. Chem. Soc. 124 (2002) 2212-2220. doi: 10.1021/ja012124x
1. [1]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
2. [2]
  Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO₂ catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
3. [3]
  Huixian Weng , Lefei Hu , Lei Hu , Yihan Zhou , Aohua Wang , Ning Wang , Wenzhe Li , Chunliu Zhu , Shiyan Guo , Miaorong Yu , Yong Gan . Corrigendum to "The complexation of insulin with sodium N-[8-(2-hydroxybenzoyl)amino]-caprylate for enhanced oral delivery: Effects of concentration, ratio, and pH" [Chinese Chemical Letters 33 (2022) 1889-1894]. Chinese Chemical Letters, 2025, 36(8): 111316-. doi: 10.1016/j.cclet.2025.111316
4. [4]
  Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
5. [5]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
6. [6]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
7. [7]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
8. [8]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
9. [9]
  Yihao He , Ru Guo , Lu Yang , Ling Li , Tong Zhang , Bing Wang , Yongzhuo Huang . Phospholipid complex-based microemulsion for treating concurrence of primary sclerosing cholangitis and inflammatory bowel disease via gut-liver crosstalk. Chinese Chemical Letters, 2025, 36(10): 110778-. doi: 10.1016/j.cclet.2024.110778
10. [10]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
11. [11]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
12. [12]
  Tian-Zhang Wang , Le-Yu Tang , Yu-Qiu Guan , Lingfei Hu , Gang Lu , Yu-Feng Liang . Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation. Chinese Chemical Letters, 2025, 36(11): 111050-. doi: 10.1016/j.cclet.2025.111050
13. [13]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
14. [14]
  Chengyao Zhao , Jingyuan Liao , Yuxiang Zhu , Yiying Zhang , Lianjie Zhai , Junrong Huang , Hengzhi You . Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles. Chinese Chemical Letters, 2025, 36(6): 110337-. doi: 10.1016/j.cclet.2024.110337
15. [15]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
16. [16]
  Jianbao Mei , Bei Li , Shu Zhang , Dongdong Xiao , Pu Hu , Geng Zhang . Enhanced Performance of Ternary NASICON-Type Na_3.5−xMn_0.5V_1.5−xZr_x (PO₄)₃/C Cathodes for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(12): 2407023-0. doi: 10.3866/PKU.WHXB202407023
17. [17]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
18. [18]
  Cong-Bin Ji , Ding-Xiong Xie , Mei Chen , Ye-Ying Lan , Bao-Hua Zhang , Ji-Ying Yang , Zheng-Hui Kang , Shu-Jie Chen , Yu-Wei Zhang , Yun-Lin Liu . Green synthesis of 2-trifluoromethylquinoline skeletons via organocatalytic N-[(α-trifluoromethyl)vinyl]isatins CN bond activation. Chinese Chemical Letters, 2025, 36(7): 110598-. doi: 10.1016/j.cclet.2024.110598
19. [19]
  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
20. [20]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1426)
HTML views(170)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142