Citation: Han Man-Yi, Pan Hong, Yao Ziyun, Li Qi. n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4274-4283. doi: 10.6023/cjoc202005093 shu

n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction

School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000

Corresponding author: Han Man-Yi, hanmy10@126.com
Received Date: 31 May 2020
Revised Date: 11 July 2020
Available Online: 5 August 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21602073), the Natural Science Foundation of Anhui Province (No. 1708085QB39) and the Young Scholars in Wanjiang Scholars Program of Anhui Provincethe Natural Science Foundation of Anhui Province 1708085QB39the National Natural Science Foundation of China 21602073

Figures(4)

A novel Brook rearrangement/alkylation reaction sequence of tertiary α-silyl alcohols has been developed using n-Bu₄NBr as the phase transfer catalyst (PTC). A number of tertiary α-silyl alcohols are applicable to the reaction, affording the products with a quaternary carbon center in high yields (up to 71%). Moreover, the carbanions generated after the Brook rearrangement could be stabilized by the electron-withdrawing group, depressing the Brook rearrangement/protonation reaction.
- phase transfer catalysis,
- bimolecular nucleophilic substitution (S_N2) reaction,
- alkylation,
- Brook rearrangement
1. [1]
  Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. doi: 10.1021/ja01541a026
2. [2]
  For selected reviews, see: (a) Lee, N.; Tan, C.-H. Asian J. Org. Chem. 2019, 8, 25.
  (b) Yabushita, K.; Yuasa, A.; Nagao, K.; Ohmiya, H. J. Am. Chem. Soc. 2019, 141, 113.
  (c) Eppe, G.; Didier, D.; Marek, I. Chem. Rev. 2015, 115, 9175.
  (d) Zhang, H. -J.; Priebbenow, D. L.; Bolm, C. Chem. Soc. Rev. 2013, 42, 8540.
  (e) Boyce, G. R.; Greszler, S. N.; Johnson, J. S.; Linghu, X.; Malinowski, J. T.; Nicewicz, D. A.; Satterfield, A. D.; Schmitt, D. C.; Steward, K. M. J. Org. Chem. 2012, 77, 4503.
  (f) Smith, Ⅲ, A. B., Wuest, W. M. Chem. Commun. 2008, 45, 5883.
  (g) Moser, W. H. Tetrahedron 2001, 57, 2065.
  (h) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A. J. Organomet. Chem. 1998, 567, 181.
  (i) Bulman-Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147.
  (j) Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
3. [3]
  Greszler, S. N.; Johnson, J. S. Org. Lett. 2009, 11, 827. doi: 10.1021/ol802828d
4. [4]
  Greszler, S. N.; Johnson, J. S. Angew. Chem., Int. Ed. 2009, 48, 3689. doi: 10.1002/anie.200900215
5. [5]
  For selected examples, see: (a) Yao, M.; Lu, C.-D. Org. Lett. 2011, 13, 2782.
  (b) Han, X.-J.; Yao, M.; Lu, C.-D. Org. Lett. 2012, 14, 2906.
6. [6]
  Luzzio, F. A. Tetrahedron 2001, 57, 915. doi: 10.1016/S0040-4020(00)00965-0
7. [7]
  For selected reviews and examples, see: (a) Adero, P. O.; Amarasekara, H.; Wen. P.; Bohé L.; Crich, D. Chem. Rev. 2018, 118, 8242.
  (b) Hamlin, T. A.; Swart, M. F.; Bickelhaupt, M. ChemPhysChem 2018, 19, 1315.
  (c) Fu, G. C. ACS Cent. Sci. 2017, 3, 692.
  (d) Phan, T. B.; Nolte, C.; Kobayashi, S.; Ofial, A. R.; Mayr, H. J. Am. Chem. Soc. 2009, 131, 11392.
  (e) Marshall, J. A. Chem. Rev. 1989, 89, 1503.
8. [8]
  Kato, M.; Mori, A.; Oshino, H.; Enda, J.; Kobayashi, K.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1773. doi: 10.1021/ja00318a036
9. [9]
  Collados, J. F.; Ortiz, P.; Perez, J. M.; Xia, Y.; Koenis, M. A. J.; Buma, W. J.; Nicu, V. P.; Harutyunyan, S. R. Eur. J. Org. Chem. 2018, 2018, 3900.
10. [10]
  For selected reviews and examples, see: (a) Collados, J. F.; Ortiz, P.; Harutyunyan, S. R. Eur. J. Org. Chem. 2016, 3065.
  (b) Leibeling, M.; Shurrush, K. A.; Werner, V.; Perrin, L.; Marek, I. Angew. Chem., Int. Ed. 2016, 55, 6057.
11. [11]
  For selected reviews and examples, see: (a) Zong, L.; Tan, C.-H. Acc. Chem. Res. 2017, 50, 842.
  (b) Albanese, D. C. M.; Foschi, F.; Penso, M. Org. Process Res. Dev. 2016, 20, 129.
  (c) Kaneko, S.; Kumatabara, Y.; Shirakawa, S. Org. Biomol. Chem. 2016, 14, 5367.
  (d) Shirakawa, S.; Maruoka, K. Angew. Chem., Int. Ed. 2013, 52, 4312.
  (e) Takeda, K.; Ohnishi, Y. Tetrahedron Lett. 2000, 41, 4169.
  (f) Ando, M.; Sasaki, M.; Miyashita, I.; Takeda, K. J. Org. Chem. 2015, 80, 247.
12. [12]
  For selected examples, see: (a) Han, M.-Y.; Pan, H.; Li, P.; Wang, L. J. Org. Chem. 2020, 85, 5825.
  (b) Pan, H.; Han, M.-Y.; Li, P.; Wang, L. J. Org. Chem. 2019, 84, 14281.
  (c) Han, M.-Y.; Luan, W.-Y.; Mai, P.-L.; Li, P.; Wang, L. J. Org. Chem. 2018, 83, 1518.
  (d) Han, M.-Y.; Lin, J.; Li, W.; Luan, W.-Y.; Mai, P.-L.; Zhang, Y. Green Chem. 2018, 20, 1228.
  (e) Han, M.-Y.; Pan, H.; Lin, J.; Li, W.; Li, P.; Wang, L. Org. Biomol. Chem. 2018, 16, 4117.
  (f) Han, M.-Y.; Xie, X.; Zhou, D.; Li, P.; Wang, L. Org. Lett. 2017, 19, 2282.
  (g) Han, M.-Y.; Yang, F.-Y.; Zhou, D.; Xu, Z. Org. Biomol. Chem. 2017, 15, 1418.
13. [13]
  For selected examples, see: (a) Deng, Y.; Liu, Q.; Smith, Ⅲ, A. B. J. Am. Chem. Soc. 2017, 139, 9487.
  (b) Zhang, F.-G.; Marek, I. J. Am. Chem. Soc. 2017, 139, 8364.
  (c) Zhang, H.; Ma, S.; Yuan, Z.; Chen, P.; Xie, X.; Wang, X.; She, X. Org. Lett. 2017, 19, 3478.
  (d) Lin, C.-Y.; Sun, Z.; Xu, Y.-J.; Lu, C.-D. J. Org. Chem. 2015, 80, 3714.
  (e) Liu, B.; Lu, C. D. J. Org. Chem. 2011, 76, 4205.
  (f) Smith, Ⅲ, A. B.; Xian, M.; Kim, W.-S.; Kim, D.-S. J. Am. Chem. Soc. 2006, 128, 12368.
  (g) Jung, M. E.; Nichols, C. J. J. Org. Chem. 1996, 61, 9065.
1. [1]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
2. [2]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
3. [3]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
4. [4]
  Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
5. [5]
  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
6. [6]
  Huizhong Wu , Ruiheng Liang , Ge Song , Zhongzheng Hu , Xuyang Zhang , Minghua Zhou . Enhanced interfacial charge transfer on Bi metal@defective Bi₂Sn₂O₇ quantum dots towards improved full-spectrum photocatalysis: A combined experimental and theoretical investigation. Chinese Chemical Letters, 2024, 35(6): 109131-. doi: 10.1016/j.cclet.2023.109131
7. [7]
  Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO₂ catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
8. [8]
  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
9. [9]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
10. [10]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
11. [11]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
12. [12]
  Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679
13. [13]
  Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
14. [14]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
15. [15]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
16. [16]
  Xinyu Guo , Chang Li , Wenjun Deng , Yi Zhou , Yan Chen , Yushuang Xu , Rui Li . Phase engineering and heteroatom incorporation enable defect-rich MoS₂ for long life aqueous iron-ion batteries. Chinese Chemical Letters, 2025, 36(3): 109715-. doi: 10.1016/j.cclet.2024.109715
17. [17]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
18. [18]
  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
19. [19]
  Quanyou Guo , Yue Yang , Tingting Hu , Hongqi Chu , Lijun Liao , Xuepeng Wang , Zhenzi Li , Liping Guo , Wei Zhou . Regulating local electron transfer environment of covalent triazine frameworks through F, N co-modification towards optimized oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(1): 110235-. doi: 10.1016/j.cclet.2024.110235
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(39)
Abstract views(3536)
HTML views(472)

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

n-Bu4NBr Catalyzed Brook Rearrangement/Alkylation Reaction

Metrics

通讯作者: 陈斌, bchen63@163.com

n-Bu₄NBr Catalyzed Brook Rearrangement/Alkylation Reaction